Design, Synthesis and Antiviral Activity of Indole Derivatives Containing Quinoline Moiety

Design, Synthesis and Antiviral Activity of Indole Derivatives Containing Quinoline Moiety | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Design, Synthesis and Antiviral Activity of Indole Derivatives Containing Quinoline Moiety Bangcan He, Yuzhi Hu, Yishan Qin, Yufang Zhang, Xingping Luo, and 2 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-3964276/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 24 Jul, 2024 Read the published version in Molecular Diversity → Version 1 posted 12 You are reading this latest preprint version Abstract A series of indole derivatives containing quinoline structure were designed and synthesized. The synthesized compounds were characterized by NMR and HRMS. And W14 was performed by single crystal X-ray diffraction experiments. The antiviral activity studies showed that some of the target compounds possessed significant activity against tobacco mosaic virus (TMV). In particular, W20 had significant activity. The results of in vivo anti-TMV activity assay showed that W20 possessed the best curative and protective activities with EC 50 values of 84.4 and 65.7 µ g/mL, which were better than ningnanmycin (NNM) 205.1 and 162.0 µ g/mL, respectively. The results of Microscale thermophoresis (MST) showed that W20 had a strong binding affinity for the tobacco mosaic virus coat protein (TMV-CP) with a dissociation constant (K d ) of 0.00519 µ mol/L, which was superior to that of NNM (1. 65320 µ mol/L). The molecular docking studies were accordance with the experimental results. In addition, the determination of malondialdehyde (MDA) content in tobacco leaves showed that W20 improved the disease resistance of tobacco. Overall, this study shows that indole derivatives containing quinoline can be used as new antiviral agents for plant viruses for further research. indole quinoline tobacco mosaic virus Antiviral activity Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Figure 8 1 Introduction Tobacco mosaic virus (TMV) can infect tobacco, tomato, pepper and other crops [ 1 – 4 ]. Once infected, the plant was difficult to cure and severely affects the quality and yield of tobacco [ 5 ]. It was one of the most studied viruses in the world [ 6 ]. The long-term use of traditional antiviral drugs such as NNM and ribavirin had led to varying degrees of resistance to plant viruses [ 7 , 8 ]. It had caused serious problems such as environmental pollution, increased resistance, and pesticide residues [ 9 – 11 ]. Therefore, new types of pesticides are the trend, and it was important to develop high efficiency, low toxicity, easy degradation, environmentally friendly and wide range of biological activity pesticides. Indole (Fig. 1 ) was a nitrogen-containing benzopyrrole alkaloid found not only in natural plants such as chimonanthus praecox, oleander, jasmine, croton root, citrus and orange blossoms [ 12 , 13 ], but also in many animals and marine organisms [ 14 ]. With the progress of science and technology and the development of human life sciences, a series of indole derivatives had been synthesized by structural modification using indole as a starting point. Subsequent studies had revealed that indole derivatives had remarkable biological activities, and their derivatives had attracted attention for their good antibacterial [ 15 – 17 ], antiviral [ 18 – 21 ], antioxidant [ 22 ], anti-inflammatory [ 23 ], anticancer [ 24 ], antitumor [ 25 ], protein kinase inhibitory properties [ 26 ] and these derivatives had been widely used in pesticides, pharmaceuticals, dyestuffs, and fragrances, among other industries. Quinolines [ 27 ] (Fig. 1 ), also known as benzopyridines, had a bicyclic structure and are N -heterocyclic aromatic compounds. Quinolines and isoquinolines obtained from natural products, this class of compounds had attracted much attention from researchers due to its simple chemical structure and remarkable biological activity [ 28 ]. Quinoline was a naturally active alkaloid [ 29 ]. It had received wide attention due to its favorable antibacterial [ 30 , 31 ], antitubercular [ 32 ], anticancer [ 33 ] and other biological activities. In which Fig. 2 shows a commercial medicament containing quinoline. Therefore, a series of indole derivatives containing quinoline were designed and synthesized by active splicing principle in this study. The design idea of the target compounds was shown in Fig. 3 Preliminary bioactivity tests showed that some of the compounds possessed good antiviral activity. Among them, W20 showed significant inhibitory activity against TMV. Meanwhile, MST and molecular docking indicated that the compound for W20 had strong binding ability against TMV CP. Figure 1 Figure 2 Figure 3 2 Results and discussion 2.1 Chemistry Scheme 1 The synthesis of the target compounds was carried out as shown in Scheme 1 and the synthesized compounds were characterized by NMR and HRMS. Intermediate 1 was obtained by reacting various substituted benzoyl chloride with o-aminoacetophenone. Secondly, intermediate 1 was dissolved in 1,4-dioxane and reacted with sodium hydroxide as acid-binding agent to produce intermediate 2 by refluxing at 110 ℃, and then intermediate 2 was reacted with diphosphorus pentasulfide to obtain intermediate 3 . Further, intermediate 4 was obtained by using substituting indole as a raw material and refluxing with bromopropylene oxide under alkaline condition by heating at 45 ℃ for 12 h. Finally, K 2 CO 3 and 20 mL of DMF were added to a round bottom flask along with Intermediate 4 and after 0.5 h, Intermediate 3 was added to the reaction mixture. The reaction was followed by TLC at 77°C for about 10 h. It was then mixed with 90 mL of distilled water and extracted with ethyl acetate. The lower liquid phase was recovered, dried, filtered and washed three times with saturated brine to remove the ethyl acetate solvent. Finally, W1-W21 was purified by column chromatography (petroleum ether: ethyl acetate = 15:1, v/v ). 2.2 Spectral characteristic of title compounds W1-W21 was confirmed on NMR and HRMS spectra. Take W3 as an example: In the 1 H NMR spectrum, the double peak at δ 7.36 was attributed to the existence of H in the 2-position of indole ring. The double peak at δ 6.40 was attributed to the existence of H in the 3-position of indole ring. And the double peak at δ 5.69 was attributed to the existence of -OH in the aliphatic chain. The two high frequency quadruple peaks of δ 4.46 and δ 4.25 are attributed to the existence of aliphatic chain (- CH 2 CH(OH)CH 2 -) connected with indole ring. The multiple peaks of δ 4.20–4.13 are attributed to the existence of aliphatic chain (-CH 2 CH (OH)CH 2 -) connected with indole ring. The two high frequency quadruple peaks of δ 3.44 and δ 3.23 are attributed to the existence of aliphatic chain (-CH 2 CH(OH) CH 2 - ) linked to indole ring. In 13 C NMR spectrum, δ 127.49 was attributed to the existence of C in position 2 of indole ring. And δ 101.08 was attributed to the existence of C in position 3 of indole ring. The three signal peaks at δ 51.49 and δ 35.90 were attributed to the existence of C on the aliphatic chain (-CH 2 CH(OH)CH 2 -) linked to the indole ring. The obvious single-line peak at δ -116.46 in 19 F NMR spectrum confirmed the existence of F in benzene ring of indole structure. In the HRMS spectrogram, the target product's HRMS [M + H] + Calcd for C 26 H 21 FN 2 OS 429.14313, found 429.14314. The measured value and theoretical calculation value (m/z 0.0030) are within the error range, and the structure of the target compound W20 was further confirmed. Detailed data are included in the Supporting Information . In addition, in order to further determine the structure of the target compound, W14 was analyzed by single crystal X-ray diffraction, and further determined the structure of indole derivatives containing quinoline. The crystal structure (Fig. 4 ) and data (CCDC: 2269080) can be obtained by accessing the Cambridge Crystal Database. More characterization data are provided in the Supporting Information . Figure 4 2.3 Antiviral activity Half-leaf spot method was employed to investigate the antiviral activity of target compounds on Nicotiana tabacum leaves grown at the same age and TMV (500 µ g/mL) [ 34 – 37 ]. The results are shown in Table 1 and Fig. 5 that the concentration was 500 µ g/mL, the inhibition rates of W7 , W16 , W18 , W20 and W21 were 75.2, 64.5, 68.4, 75.1 and 65.9%, respectively, in terms of curative activity, which were superior to the control agent NNM (61.3%). The inhibition rates of compounds W7 , W8 , W16 , W17 , W18 , W20 and W21 were 79.9, 68.3, 66.5, 71.8, 75.3, 82.7 and 67.3%, respectively, in terms of protective activity, which were better than the control agent NNM (66.0%). When it came to inactivation activity, the inhibition rates of W7 , W18 and W20 were 68.1, 67.9 and 71.7%, which were close to the control agent NNM (82.2%). Table 1 Antiviral activities of the target compounds against TMV at 500 µ g/mL in vivo a Compd. R 1 R 2 Curative activity (%) a Protection activity (%) a Inactivation activity (%) a W1 H 2-Cl 53.8 ± 2.9 54.6 ± 4.1 46.3 ± 3.5 W2 H 4-Cl 53.8 ± 2.7 59.9 ± 2.8 50.9 ± 3.7 W3 H 2-F 46.4 ± 4.8 52.9 ± 4.4 45.9 ± 2.9 W4 H 3-CH 3 52.7 ± 1.2 55.1 ± 6.2 50.3 ± 2.5 W5 H 4-CH 3 49.1 ± 3.3 64.0 ± 2.7 45.2 ± 3.2 W6 H 3-OCH 3 51.6 ± 2.0 59.3 ± 1.1 53.4 ± 1.3 W7 5-Br H 75.2 ± 3.8 79.9 ± 1.3 68.1 ± 4.5 W8 5-Br 2-Cl 62.1 ± 3.5 68.3 ± 2.0 47.5 ± 4.5 W9 5-Br 4-Cl 46.1 ± 2.0 51.2 ± 3.5 39.6 ± 4.1 W10 5-Br 4-CH 3 50.8 ± 4.9 61.1 ± 1.3 48.5 ± 4.0 W11 5-Cl H 42.0 ± 1.9 61.0 ± 4.4 51.0 ± 0.7 W12 5-Cl 4-CF 3 59.1 ± 5.0 63.4 ± 2.2 57.2 ± 5.0 W13 5-Cl 2,4-di-Cl 51.7 ± 5.7 53.0 ± 4.8 45.1 ± 4.7 W14 5-Cl 4-Cl 40.8 ± 2.6 47.3 ± 4.5 38.7 ± 4.1 W15 5-Cl 4-CH 3 54.6 ± 4.5 61.1 ± 1.2 48.2 ± 1.8 W16 5-OCH 3 H 64.5 ± 2.8 66.5 ± 2.1 56.1 ± 2.9 W17 5-OCH 3 3-CH 3 58.6 ± 2.8 71.8 ± 2.2 55.0 ± 3.2 W18 5-OCH 3 4-CH 3 68.4 ± 3.4 75.3 ± 1.2 67.9 ± 1.6 W19 5-OCH 3 4-Cl 56.4 ± 3.4 61.5 ± 2.5 52.5 ± 4.6 W20 5-OCH 3 3-OCH 3 75.1 ± 3.5 82.7 ± 0.4 71.7 ± 6.6 W21 5-OCH 3 4-CF 3 65.9 ± 2.2 67.3 ± 2.4 56.1 ± 4.7 ningnanmycin b - - 61.3 ± 4.3 66.0 ± 3.1 82.2 ± 0.8 a Average values of three replicates. b The commercial antiviral agents ningnanmycin. To further confirm the antiviral activity of our target compounds, the EC 50 value were tested for some compounds (Table 2 ). The results show that the EC 50 value of W7 , W18 , W20 and W21 were 86.6, 137.3, 84.4 and 168.4 µ g/mL, respectively, in terms of curative activity, which were superior to the control agent NNM (205.1 µ g/mL). The EC 50 value of W7 , W8 , W16 , W17 , W18 , W20 and W21 were 76.8, 119.9, 162.7, 101.4, 96.3, 65.7 and 119.6 µ g/mL, respectively, in terms of protective activity, which were better than NNM (162.0 µ g/mL). Table 2 The EC 50 values of several target compounds against TMV a Compd. Regression equation r 2 EC 50 (µg/mL) Curative activity W7 y = 0.6920x + 3.6591 0.9964 86.6 W18 y = 0.8773x + 3.1245 0.9919 137.3 W20 y = 0.7619x + 3.5323 0.9864 84.4 W21 y = 0.7720x + 3.2813 0.9810 168.4 ningnanmycin b y = 0.8089x + 3.1299 0.9943 205.1 Protection activity W7 y = 0.7983x + 3.4947 0.9961 76.8 W8 y = 0.6218x + 3.7073 0.9722 119.9 W16 y = 0.7487x + 3.3443 0.9996 162.7 W17 y = 0.8257x + 3.3437 0.9943 101.4 W18 y = 0.7548x + 3.5028 0.9970 96.3 W20 y = 0.8500x + 3.4548 0.9824 65.7 W21 y = 0.6546x + 3.6398 0.9846 119.6 ningnanmycin b y = 0.5410x + 3.8046 0.9908 162.0 a Average values of three replicates. b The commercial antiviral agents ningnanmycin. Table 1 Figure 5 Table 2 2.4 Structure-activity relationship of antiviral activity From the test data of antiviral activity, it can be seen that substituents had great influence on the biological activity of compounds. According to the anti-TMV activity shown in Table 1 , the structure-activity relationship (SAR) was analyzed. H, -OCH 3 , -CF 3 and -CH 3 groups at the R position are beneficial to the curative and protective activities of the target compound against TMV. For example, the curative activities of W7 (R 1 = 5-Br, R 2 = H), W16 (R 1 = 5-OCH 3 , R 2 = H), W18 (R 1 = 5-OCH 3 , R 2 = 4-CH 3 ), W20 (R 1 = 5-OCH 3 , R 2 = 3-OCH 3 ) were 75.2, 64.5, 68.4 and 75.1%, respectively. The protective activities were 79.9, 66.5, 75.3 and 82.7%, respectively, which were superior to other substituents. It was worth noting that when R 1 = 5-OCH 3 and R 2 = 3-OCH 3 , the curative and protective effects are the best. For example, the curative and protective activities are W20 (R 1 = 5-OCH 3 , R 2 = 3-OCH 3 ) > W7 (R 1 = 5-Br, R 2 = H) > W19 (R 1 = 5-OCH 3 , R 2 = 4-Cl-Ph) > W14 (R 1 = 5-Cl, R 2 = 4-Cl-Ph). To sum up, W20 (R 1 = 5-OCH 3 , R 2 = 3-OCH 3 ) had obvious inhibitory effect on TMV. It was speculated that when R 1 and R 2 are electron donor groups, the curative and protective activities of the target compound on TMV can be enhanced. On the contrary, when there was an electron-withdrawing group, its antiviral activity decreases, which can provide an idea of structure-activity relationship. 2.5 Binding ability of W18 , W20 and NNM to TMV-CP The inhibitory effects of W18 , W20 and NNM on TMV-CP were studied by microscale thermophoresis (MST) [ 38 , 39 ], and the results were shown in Table 3 and Fig. 6 . The dissociation constants K d of W18 , W20 and NNM for TMV-CP are 0.38099 ± 0.13752 µ mol/L, 0.00519 ± 0.00259 µ mol/L and 1.65320 ± 0.42835 µ mol/L, respectively. Therefore, the affinity of W20 for TMV-CP was better than that of W18 , and far exceeds that of NNM. The results show that W20 > W18 > NNM, which was consistent with the preliminary screening results. Table 3 The dissociation constant of W18 , W20 and ningnanmycin with TMV-CP Compounds Kd ( µ M) W18 0.38099 ± 0.13752 W20 0.00519 ± 0.00259 ningnanmycin a 1. 65320 ± 0.42835 a The commercial antiviral agents ningnanmycin. Table 3 Figure 6 . 2.6 Molecular docking of W20 and NNM with TMV‑CP In order to identify TMV-CP recognition sites in W20 and NNM (protein database (PDB) code: 1EI7) [ 35 , 40 , 41 ], the results of molecular docking are shown in Fig. 7 . W20 and NNM are bound to TMV-CP in the same active pocket. Among them, W20 has a strong interaction with surrounding residues SER138 (2.83Å), TYR139 (4.67 and 5.20 Å), VAL260 (3.84 and 5.28 Å), GLN257 (0.99 Å), SER255 (2.53 Å), LYS268 (2.46 and 2.67Å), LYS253 (4.09 Å), ASP219 (2.74 Å), GLU222 (2.35Å), GLU131 (2.76 Å), VAL75 (4.56 Å), ARG134 (5.21 Å), ASP266 (4.90 Å) and GLY135 (4.97 Å) in TMV-CP active pocket through conventional hydrogen bond, carbon hydrogen bond, pi-anion and hydrophobic interaction, in which residue LYS268 (2.46 Å), ASP219 (2.74 Å), SER138 (2.83Å), GLU222 (2.35Å) and GLU131 (2.76 Å) and W20 form four strong hydrogen bonds respectively. For commercial NNM, in the active pocket of TMV-CP, it interacts with the surrounding residue GLY135 (2.70 Å), SER138 (2.76, 2.53 and 2.59Å), GLY137 (2.45 Å), SER255 (3.00 Å), ARG134 (1.79 and 2.96 Å), LYS253 (5.16 Å), GLU131 (3.64Å) and PRO254 (1.97 Å) through hydrogen bonding with residue SER138 (2.76, 2.53 and 2.59Å), GLY137 (2.45 Å) and ARG134 (1.79 and 2.96 Å), pi-alkyl and pi-anion. Through the analysis of the above results, the length of the conventional hydrogen bond formed by W20 and TMV-CP was close to that of NNM, but the number of amino acid residues of W20 and TMV-CP was more than that of NNM, which makes the antiviral activity of W20 and TMV-CP better than that of NNM through various modes of action such as carbon hydrogen bond, van der waals, pi-cation, pi-sulfur, pi-pi stacked, alkyl, pi-alkyl and hydrophobic interaction. Figure 7 2.7 Analysis characteristics of virus malondialdehyde (MDA) content of W20 Malondialdehyde (MDA) content reflects the degree of membrane lipid peroxidation caused by tobacco infestation [ 42 , 43 ]. Changes in MDA content in each test group at days 1, 3, 5 and 7 after inoculation are shown in Fig. 8 . After inoculation with TMV, the MDA content in tobacco treated with W20 gradually decreased from from the 1–5 d, reached the lowest value at the 5 d, and began to increase from the 5 to 7 d. Especially on the 5 d, the MDA content of W20 + TMV group was about 50% lower than that of CK + TMV group. In addition, the MDA content in the W20 group was also lower than that in the CK group within 1–7 d. Therefore, W20 can reduce the content of MDA in tobacco plants, effectively prevent TMV infection and reinfection, and improve tobacco disease resistance. Figure 8 . 3 Conclusion To sum up, a series of indole derivatives containing quinoline were synthesized based on the principle of active splicing, and their biological activities were tested. The results of antiviral test show that most compounds had obvious therapeutic, protective and inactivation effects on TMV. The results show that the EC 50 value of W7 , W18 , W20 and W21 were 86.6 , 137.3 , 84.4 and 168.4 µ g/mL, respectively, in terms of curative activity, which were superior to the control agent NNM (205.1 µ g/mL). The EC 50 value of W7 , W8 , W16 , W17 , W18 , W20 and W21 were 76.8, 119.9, 162.7, 101.4, 96.3, 65.7 and 119.6 µ g/mL, respectively, in terms of protective activity, which were better than NNM (162.0 µ g/mL). The results of MST showed that the K d value of W20 combined with TMV-CP was 0.00519 µ mol/L, which was better than that of control drug NNM (1.65320 mol/L). The molecular docking study was consistent with the experimental results. Moreover, W20 can reduce the malondialdehyde content of tobacco plants, effectively prevent TMV infection and reinfection, and improve tobacco disease resistance. Therefore, we can further develop indole derivatives containing quinoline as potential drugs, and also provide new ideas and certain theoretical basis for the creation of green pesticides. 4 Materials and methods 4.1 Instruments and chemicals The melting point of the compound was determined by the X-4B (Shanghai Instrument, Electrophysical and Optical Instrument Co., Ltd., China) microscopic digital melting point tester. 1 H, 13 C and 19 F NMR spectra were obtained by JEOL-ECX500 (Japanese electronics co., LTD, Japan) and ASCEND400 (Bruker, Germany), and high-resolution mass spectrometry was obtained by Thermo Scientic Q Exactive (Thermo Fisher Scientific, USA) high-resolution mass spectrometer. The N-5000 UV spectrophotometer (Shanghai Yoke Instrument Co., Ltd., China) was used to detect malondialdehyde (MDA) content. the data of the crystal were collected by an X-ray diffractometer (Bruker, Germany). All reagents and solvents were commercially purchased and were analytically pure, with no purification required and ready for use. Thin layer chromatography (TLC) analysis was performed using a WFH-203B (Shanghai Jinko Industry Co., Ltd., China) ultraviolet analyzer. 4.2 General synthetic procedure for key intermediates 1–4 4.2.1 Synthesis of intermediate 1 1-(2-aminophenyl)ethan-1-one (7.40 mmol) and 30 mL of dichloromethane were added to a round-bottomed flask, and substituted benzoyl chloride (8.88 mmol) was slowly added under magnetic stirring. At the end of the reaction 90 mL of water was added and extracted with dichloromethane in three fractions, after collecting the organic phase and removing the solvent under vacuum. Then recrystallized in ( V (petroleum ether): V (ethyl acetate) = 4:1) mixed solvent to obtain white needle-like crystals of intermediate 1. 4.2.2 Synthesis of intermediate 2 Intermediate 1 (3.95 mmol) and 1,4-dioxane (30 mL) were placed in a three-necked flask and stirred at reflux for 2 h at 110°C with the addition of NaOH (11.84 mmol). After completion of the reaction, the solvent was removed under vacuum and the reaction mixture was added to about 200 mL of H 2 O, 10% aqueous HCl was added into the above mixture until pH 6–7, filtered by pumping, and then the residue was washed with H 2 O and a mixture of dichloromethane and ethyl acetate ( V : V = 1:1) to give Intermediate 2 . 4.2.3 Synthesis of intermediate 3 Intermediate 2 (4.25 mmol) and anhydrous pyridine (30 mL) were placed in a three-necked flask, diphosphorus pentasulfide (8.50 mmol) was slowly added to the mixture and the reaction system was refluxed at 110°C for about 5 h. After completion of the reaction, the reaction mixture was added to about 200 mL of H 2 O and stirred for a few minutes, the mixture was filtered and the solid product obtained was dried at 40°C for 6 h. The crude product was completely dissolved in 200 mL of 10% sodium hydroxide solution, and glacial acetic acid was added to the above mixture until the pH 6–7. After filtration, the residue was washed with H 2 O and petroleum ether to give intermediate 3 [ 44 , 45 ]. 4.2.4 Synthesis of intermediate 4 A round-bottomed flask containing of substituted indole (1.53 mmol) and 15 mL DMF was filled with the mixture. Stirring continuously, NaH (4.59 mmol) was gradually added, and after 20 min of stirring, epibromohydrin (4.59 mmol) was added. The mixture was then heated to 45°C and refluxed for a duration of 12 h. Following heating, the reactant was mixed with 90 milliliters of distilled water and extracted three times using ethyl acetate. To produce oily compound intermediate 4 , gather the lower liquid, wash it three times with saturated brine, and then dry, filter, and spin-dry it [ 46 ]. 4.2.5 Synthesis of target compounds W1-W21 K 2 CO 3 (13.86 mmol) and 20 mL of DMF were added to a round-bottom flask along with Intermediate 4 (4.62 mmol). Intermediate 3 (5.08 mmol) was added to the reaction mixture after 0.5 h. TLC was used to track the reaction's course for around 10 h at 77°C. TLC was used to carry out the reaction. The reaction was heated, then combined with 90 mL of distilled water and extracted with ethyl acetate. The lower liquid phase was recovered, dried, filtered, and the ethyl acetate solvent was removed after three washes with saturated brine. The resultant product was purified further by column chromatography using a volumetric ratio of petroleum ether to ethyl acetate (15:1) as eluent to obtain W1-W21 ranging from 29–77%. 1-((2-(2-chlorophenyl)quinolin-4-yl)thio)-3-(1 H -indol-1-yl)propan-2-ol (W1) . White solid; yield: 42%; m.p. 154.4-155.1 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.17 (d, J = 8.0 Hz, 1H, Ph-H), 8.04 (d, J = 8.2 Hz, 1H, Ph-H), 7.87–7.77 (m, 1H, Ph-H), 7.73–7.63 (m, 1H, Ph-H), 7.69–7.60 (m, 2H, Ph-H), 7.57 (s, 1H, Ph-H), 7.57–7.47 (m, 3H, Ph-H), 7.47 (d, J = 8.2 Hz, 1H, Indol-2-H), 7.35 (d, J = 3.1 Hz, 1H, Ph-H), 7.08–6.98 (m, 1H, Ph-H), 6.97 (t, J = 7.0 Hz, 1H, Ph-H), 6.37 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.68 (d, J = 5.6 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.44 (dd, J = 15.0, 1H, - CH 2 CH(OH)CH 2 -), 4.24 (dd, J = 15.0, 1H, - CH 2 CH(OH)CH 2 -), 4.20–4.12 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.36 (dd, J = 10.0, 1H, -CH 2 CH(OH) CH 2 - ), 3.21 (dd, J = 15.0, 1H,-CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 156.18 (s), 146.83 (s), 146.67 (s), 139.32 (s), 136.14 (s), 131.74 (s), 131.59 (s), 130.52 (s), 130.39 (s), 129.98 (s), 129.58 (s), 128.16 (s), 127.48 (s), 127.14 (s), 124.78 (s), 123.25 (s), 121.01 (s), 120.47 (s), 119.03 (s), 117.26 (s), 110.05 (s), 100.66 (s), 68.23 (s), 51.01 (s), 35.38 (s); ESI-HRMS calcd for C 26 H 21 ClN 2 OS [M་H] ་ 445.11386, found 445.11359. 1-((2-(4-chlorophenyl)quinolin-4-yl)thio)-3-(1 H -indol-1-yl)propan-2-ol ( W2 ). White solid; yield: 37%; m.p. 147.5-180.3 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.27–8.22 (m, 2H, Ph-H), 8.14 (d, J = 8.0 Hz, 1H, Ph-H), 8.05 (d, J = 8.2 Hz, 1H, Ph-H), 7.84 (s, 1H, Ph-H), 7.82–7.78 (m, 1H, Ph-H), 7.66–7.60 (m, 3H, Ph-H), 7.55–7.48 (m, 2H, Ph-H), 7.40 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.05–6.96 (m, 2H, Ph-H), 6.44 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.72 (d, J = 5.6 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.49 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.27 (dd, J = 10.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.19–4.13 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.53 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.34 (dd, J = 10.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 154.07 (s), 148.12 (s), 146.78 (s), 137.44 (s), 136.12 (s), 134.74 (s), 130.52 (s), 130.01 (s), 129.73 (s), 129.23 (s), 128.91 (s), 128.22 (s), 126.83 (s), 125.07 (s), 123.27 (s), 120.99 (s), 120.53 (s), 119.05 (s), 113.42 (s), 110.02 (s), 100.68 (s), 68.36 (s), 51.19 (s), 35.46 (s); ESI-HRMS calcd for C 26 H 21 ClN 2 OS [M་H] ་ 445.11359, found 445.11359. 1-((2-(2-fluorophenyl)quinolin-4-yl)thio)-3-(1 H -indol-1-yl)propan-2-ol ( W3 ). White solid; yield: 65%; m.p. 160.1-160.5 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.16 (d, J = 8.3 Hz, 1H, Ph-H), 8.06 (d, J = 8.2 Hz, 1H, Ph-H), 7.97–7.92 (m, 1H, Ph-H), 7.82 (t, J = 8.2 Hz, 1H, Ph-H), 7.70–7.65 (m, 2H, Ph-H), 7.61–7.55 (m, 1H, Ph-H), 7.50 (dd, J = 10.0 Hz, 2H, Ph-H), 7.44–7.38 (m, 2H, Ph-H), 7.36 (d, J = 3.2 Hz, 1H, Indol-2-H), 7.04 (t, J = 10.0 Hz, 1H, Ph-H), 6.98 (t, J = 7.4 Hz, 1H, Ph-H), 6.40 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.69 (d, J = 5.7 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.46 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.25 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.20–4.13 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.44 (dd, J = 10.0 Hz, 1H, -CH 2 CH(OH) CH 2 - ), 3.23 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 161.51 (s), 159.53 (s), 153.22 (s), 147.71 (s), 147.29 (s), 136.56 (s), 131.92 (d, J = 8.8 Hz), 130.87 (s), 130.43 (s), 130.01 (s), 128.58 (s), 127.99 (d, J = 12.5 Hz), 127.49 (s), 125.34 (d, 4 J C−F = 3.8 Hz), 125.25 (s), 123.65 (s), 121.42 (s), 120.87 (s), 119.44 (s), 117.30 (d, 3 J C−F = 6.3 Hz), 116.98 (s), 116.80 (s), 110.44 (s), 101.08 (s), 68.62 (s), 51.49 (s), 35.90 (s); 19 F NMR (470 MHz, DMSO- d 6 ) δ -116.46; ESI-HRMS calcd for C 26 H 21 FN 2 OS [M་H] ་ 429.14313, found 429.14314. 1-(1 H -indol-1-yl)-3-((2-(m-tolyl)quinolin-4-yl)thio)propan-2-ol ( W4 ). White solid; yield: 54%; m.p. 119.0-119.2 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.14 (dd, J = 10 Hz, 1H, Ph-H), 8.09 (s, 1H, Ph-H), 8.06 (d, J = 8.1 Hz, 1H, Ph-H), 7.98 (d, J = 8.2 Hz, 1H, Ph-H), 7.86 (s, 1H, Ph-H), 7.81–7.77 (m, 1H, Ph-H), 7.64–7.60 (m, 1H, Ph-H), 7.55–7.50 (m, 2H, Ph-H), 7.46 (t, J = 7.7 Hz, 1H, Ph-H), 7.40 (d, J = 3.1 Hz, 1H, Ph-H), 7.34 (d, J = 7.4 Hz, 1H, Indol-2-H), 7.04–6.95 (m, 2H, Ph-H), 6.43 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.7 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.51 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.27 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.21–4.14 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.53 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.34 (dd, J = 10.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 2.46 (s, 3H,-Ph-CH 3 ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 155.52 (s), 147.66 (s), 146.91 (s), 138.69 (s), 138.09 (s), 136.13 (s), 130.47 (s), 130.35 (s), 129.99 (s), 129.72 (s), 128.81 (s), 128.21 (s), 127.99 (s), 126.57 (s), 125.04 (s), 124.73 (s), 123.26 (s), 120.99 (s), 120.51 (s), 119.05 (s), 113.79 (s), 110.01 (s), 100.65 (s), 68.38 (s), 51.18 (s), 35.49 (s), 21.34 (s); ESI-HRMS calcd for C 27 H 24 N 2 OS [M་H] ་ 425.16818, found 425.16821. 1-(1 H -indol-1-yl)-3-((2-(p-tolyl)quinolin-4-yl)thio)propan-2-ol ( W5 ). White solid; yield: 29%; m.p. 158.0-158.3 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.13 (d, J = 8.2 Hz, 3H, Ph-H), 8.04 (d, J = 7.9 Hz, 1H, Ph-H), 7.82 (s, 1H, Ph-H), 7.80–7.76 (m, 1H, Ph-H), 7.62–7.58 (m, 1H, Ph-H), 7.54 (t, J = 8.4 Hz, 2H, Ph-H), 7.40 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.38 (d, J = 8.0 Hz, 2H, Ph-H), 7.06–6.98 (m, 2H, Ph-H), 6.44 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.7 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.50 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.28 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.21–4.14 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.51 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.33 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 2.41 (s, 3H,-Ph-CH 3 ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 155.27 (s), 147.60 (s), 146.91 (s), 139.51 (s), 136.14 (s), 135.87 (s), 130.32 (s), 129.92 (s), 129.73 (s), 129.51 (s), 128.22 (s), 127.38 (s), 126.42 (s), 124.95 (s), 123.23 (s), 121.03 (s), 120.53 (s), 119.06 (s), 113.38 (s), 110.04 (s), 100.68 (s), 68.39 (s), 51.21 (s), 35.48 (s), 21.08 (s); ESI-HRMS calcd for C 27 H 24 N 2 OS [M་H] ་ 425.16821, found 425.16821. 1-(1 H -indol-1-yl)-3-((2-(3-methoxyphenyl)quinolin-4-yl)thio)propan-2-ol ( W6 ). White solid; yield: 58%; m.p. 117.3-118.1 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.14 (dd, J = 10 Hz, 1H, Ph-H), 8.06 (d, J = 7.3 Hz, 1H, Ph-H), 7.87 (s, 1H, Ph-H), 7.84–7.82 (m, 1H, Ph-H), 7.82–7.75 (m, 1H, Ph-H), 7.65–7.60 (m, 1H, Ph-H), 7.55–7.47 (m, 1H, Ph-H), 7.55–7.47 (m, 3H, Ph-H), 7.40 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.13–7.09 (m, 1H, Ph-H), 7.05–6.96 (m, 2H, Ph-H), 6.43 (d, J = 2.5 Hz, 1H, Indol-3-H), 5.72 (d, J = 5.7 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.50 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.27 (dd, J = 10.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.21–4.13 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.88 (s, 3H, Ph-OCH 3 ), 3.54 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.35 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 159.82 (s), 155.19 (s), 147.77 (s), 146.81 (s), 140.22 (s), 136.13 (s), 130.39 (s), 130.06 (s), 130.01 (s), 129.72 (s), 128.21 (s), 126.67 (s), 125.12 (s), 123.26 (s), 121.01 (s), 120.51 (s), 119.89 (s), 119.05 (s), 115.29 (s), 113.89 (s), 112.95 (s), 110.03 (s), 100.66 (s), 68.41 (s), 55.38 (s), 51.21 (s), 35.47 (s); ESI-HRMS calcd for C 27 H 24 N 2 O 2 S [M་H] ་ 441.16312, found 441.16313. 1-(5-bromo-1 H -indol-1-yl)-3-((2-phenylquinolin-4-yl)thio)propan-2-ol ( W7 ). White solid; yield: 61%; m.p. 188.8-189.2 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.23–8.20 (m, 2H, Ph-H), 8.13 (dd, J = 10 Hz, 1H, Ph-H), 8.06 (d, J = 7.9 Hz, 1H, Ph-H), 7.85 (s, 1H, Ph-H), 7.82–7.78 (m, 1H, Ph-H), 7.73 (d, J = 2.0 Hz, 1H, Ph-H), 7.64–7.61 (m, 1H, Ph-H), 7.60–7.57 (m, 2H, Ph-H), 7.56–7.51 (m, 2H, Ph-H), 7.46 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.13 (dd, J = 5 Hz, 1H, Ph-H), 6.44 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.6 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.50 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.28 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.18–4.11 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.54 (dd, J = 10.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.32 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 155.38 (s), 147.74 (s), 146.90 (s), 138.70 (s), 134.98 (s), 131.30 (s), 130.40 (s), 130.04 (s), 130.02 (s), 129.82 (s), 128.92 (s), 127.49 (s), 126.63 (s), 125.02 (s), 123.42 (s), 123.24 (s), 122.68 (s), 113.68 (s), 112.20 (s), 111.72 (s), 100.43 (s), 68.37 (s), 51.37 (s), 35.41 (s); ESI-HRMS calcd for C 26 H 21 BrN 2 OS [M་H] ་ 489.06311, found 489.06307. 1-(5-bromo-1 H -indol-1-yl)-3-((2-(2-chlorophenyl)quinolin-4-yl)thio)propan-2-ol ( W8 ). White solid; yield: 75%; m.p. 145.3-145.9 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.16 (dd, J = 8.3, 1.3 Hz, 1H, Ph-H), 8.04 (d, J = 8.3 Hz, 1H, Ph-H), 7.84–7.80 (m, 1H, Ph-H), 7.70–7.66 (m, 2H, Ph-H), 7.65–7.62 (m, 2H, Ph-H), 7.56–7.51 (m, 3H, Ph-H), 7.47 (d, J = 8.7 Hz, 1H, Ph-H), 7.41 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.14 (dd, J = 10 Hz, 1H, Ph-H), 6.38 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.68 (d, J = 5.6 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.44 (dd, J = 10.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.24 (dd, J = 10.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.17–4.10 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.41 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.19 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 156.15 (s), 146.77 (s), 146.66 (s), 139.30 (s), 134.99 (s), 131.74 (s), 131.56 (s), 131.13 (s), 130.52 (s), 130.39 (s), 129.97 (s), 127.48 (s), 127.14 (s), 124.75 (s), 123.43 (s), 123.23 (s), 122.61 (s), 117.24 (s), 112.22 (s), 111.72 (s), 100.43 (s), 68.22 (s), 51.17 (s), 35.30 (s); ESI-HRMS calcd for C 26 H 20 BrClN 2 OS [M་H] ་ 523.02423, found 523.02410. 1-(5-bromo-1 H -indol-1-yl)-3-((2-(4-chlorophenyl)quinolin-4-yl)thio)propan-2-ol ( W9 ). White solid; yield: 72%; m.p. 162.8-163.3 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.25–8.21 (m, 2H, Ph-H), 8.13 (d, J = 8.2 Hz, 1H, Ph-H), 8.04 (d, J = 8.3 Hz, 1H, Ph-H), 7.82–7.78 (m, 2H, Ph-H), 7.72 (d, J = 2.0 Hz, 1H, Ph-H), 7.65–7.60 (m, 3H, Ph-H), 7.51 (d, J = 8.7 Hz, 1H, Ph-H), 7.46 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.14 (dd, J = 10 Hz, 1H, Ph-H), 6.44 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.6 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.48 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.28 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.18–4.11 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.52 (dd, J = 10.0 Hz, 1H, -CH 2 CH(OH) CH 2 - ), 3.33 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 154.08 (s), 148.07 (s), 146.78 (s), 137.45 (s), 134.98 (s), 134.75 (s), 131.27 (s), 130.51 (s), 130.04 (s), 130.00 (s), 129.20 (s), 128.91 (s), 126.82 (s), 125.06 (s), 123.44 (s), 123.26 (s), 122.68 (s), 113.47 (s), 112.18 (s), 111.72 (s), 100.46 (s), 68.37 (s), 51.35 (s), 35.42 (s); ESI-HRMS calcd for C 26 H 20 BrClN 2 OS [M་H] ་ 523.02423, found 523.02410. 1-(5-bromo-1 H -indol-1-yl)-3-((2-(p-tolyl)quinolin-4-yl)thio)propan-2-ol ( W10 ). White solid; yield: 63%; m.p. 166.9-167.5 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.12–8.09 (m, 3H, Ph-H), 8.03 (d, J = 8.2 Hz, 1H, Ph-H), 7.81–7.76 (m, 2H, Ph-H), 7.73 (d, J = 2.0 Hz, 1H, Ph-H), 7.62–7.58 (m, 1H, Ph-H), 7.52 (d, J = 8.7 Hz, 1H, Ph-H), 7.46 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.38 (d, J = 8.0 Hz, 2H, Ph-H), 7.14 (dd, J = 10 Hz, 1H, Ph-H), 6.44 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.5 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.49 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.28 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.18–4.11 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.52 (dd, J = 10.0 Hz, 1H, -CH 2 CH(OH) CH 2 - ), 3.30 (dd, J = 15.0 Hz, 1H, -CH 2 CH(OH) CH 2 - ), 2.42 (s, 3H,-Ph-CH 3 ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 155.28 (s), 147.53 (s), 146.91 (s), 139.48 (s), 135.89 (s), 134.98 (s), 131.28 (s), 130.31 (s), 130.04 (s), 129.91 (s), 129.52 (s), 127.35 (s), 126.41 (s), 124.93 (s), 123.46 (s), 123.22 (s), 122.68 (s), 113.45 (s), 112.19 (s), 111.73 (s), 100.44 (s), 68.34 (s), 51.38 (s), 35.42 (s), 21.07 (s); ESI-HRMS calcd for C 27 H 23 BrN 2 OS [M་H] ་ 503.07874, found 503.07872. 1-(5-chloro-1 H -indol-1-yl)-3-((2-phenylquinolin-4-yl)thio)propan-2-ol ( W11 ). White solid; yield: 52%; m.p. 156.6-157.1 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.23–8.20 (m, 2H, Ph-H), 8.13 (dd, J = 10.0 Hz, 1H, Ph-H), 8.06 (d, J = 7.9 Hz, 1H, Ph-H), 7.85 (s, 1H, Ph-H), 7.82–7.78 (m, 1H, Ph-H), 7.64–7.61 (m, 1H, Ph-H), 7.61–7.56 (m, 3H, Ph-H), 7.56–7.52 (m, 2H, Ph-H), 7.48 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.03 (dd, J = 10.0 Hz, 1H, Ph-H), 6.44 (d, J = 3.0 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.6 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.50 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.28 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.19–4.12 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.53 (dd, J = 15.0 Hz, 1H, -CH 2 CH(OH) CH 2 - ), 3.37 (dd, J = 15.0 Hz, 1H, -CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 155.38 (s), 147.74 (s), 146.90 (s), 138.70 (s), 134.75 (s), 131.45 (s), 130.38 (s), 130.02 (s), 129.82 (s), 129.32 (s), 128.90 (s), 127.48 (s), 126.62 (s), 125.02 (s), 123.76 (s), 123.24 (s), 120.90 (s), 119.63 (s), 113.67 (s), 111.71 (s), 100.51 (s), 68.39 (s), 51.39 (s), 35.42 (s); ESI-HRMS calcd for C 26 H 21 ClN 2 OS [M་H] ་ 445.11362, found 445.11359. 1-(5-chloro-1 H -indol-1-yl)-3-((2-(4-(trifluoromethyl)phenyl)quinolin-4-yl)thio)propan-2-ol ( W12 ). White solid; yield: 49%; m.p. 126.6-126.8 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.39 (d, J = 8.0 Hz, 2H, Ph-H), 8.17–8.13 (m, 1H, Ph-H), 8.08 (d, J = 8.0 Hz, 1H, Ph-H), 7.92 (d, J = 8.2 Hz, 2H, Ph-H), 7.86 (s, 1H, Ph-H), 7.85–7.80 (m, 1H, Ph-H), 7.69–7.64 (m, 1H, Ph-H), 7.57 (d, J = 2.1 Hz, 1H, Ph-H), 7.55 (d, J = 8.7 Hz, 1H, Ph-H), 7.48 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.01 (dd, J = 10.0 Hz, 1H, Ph-H), 6.44 (d, J = 2.4 Hz, 1H, Indol-3-H), 5.74 (d, J = 5.5 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.48 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.28 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.19–4.11 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.55 (dd, J = 10.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.32 (dd, J = 10.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 154.25 (s), 148.80 (s), 147.17 (s), 142.95 (s), 135.15 (s), 131.86 (s), 131.05 (s), 130.57 (s), 129.73 (s), 128.63 (s), 127.58 (s), 126.18 (s), 125.66 (s), 125.3 (dd, 3 J C−F = 4.18 Hz), 124.16 (s), 123.69 (s), 121.31 (s), 120.03 (s), 114.26 (s), 112.10 (s), 100.95 (s), 68.75 (s), 51.79 (s), 35.85 (s); 19 F NMR (470 MHz, DMSO- d 6 ) δ -60.93; ESI-HRMS calcd for C 27 H 20 ClF 3 N 2 OS [M་H] ་ 513.10107, found 513.10097. 1-(5-chloro-1 H -indol-1-yl)-3-((2-(2,4-dichlorophenyl)quinolin-4-yl)thio)propan-2-ol ( W13 ). White solid; yield: 80%; m.p. 145.5-145.9 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.15 (d, J = 7.9 Hz, 1H, Ph-H), 8.04 (d, J = 8.2 Hz, 1H, Ph-H), 7.84–7.80 (m, 2H, Ph-H), 7.72–7.64 (m, 2H, Ph-H), 7.60 (dd, J = 10.0 Hz, 1H, Ph-H), 7.54 (d, J = 2.1 Hz, 1H, Ph-H), 7.51 (d, J = 9.3 Hz, 2H, Ph-H), 7.43 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.03 (dd, J = 10.0 Hz, 1H, Ph-H), 6.39 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.69 (d, J = 5.6 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.43 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.25 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.17–4.09 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.35 (dd, J = 10.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.18 (dd, J = 10.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 155.09 (s), 147.07 (s), 146.62 (s), 138.16 (s), 134.75 (s), 134.31 (s), 132.99 (s), 132.65 (s), 131.29 (s), 130.49 (s), 129.96 (s), 129.43 (s), 129.25 (s), 127.70 (s), 127.29 (s), 124.79 (s), 123.77 (s), 123.23 (s), 120.93 (s), 119.55 (s), 117.00 (s), 111.71 (s), 100.54 (s), 68.21 (s), 51.21 (s), 35.33 (s); ESI-HRMS calcd for C 26 H 19 Cl 3 N 2 OS [M་H] ་ 513.03613, found 513.03564. 1-(5-chloro-1 H -indol-1-yl)-3-((2-(4-chlorophenyl)quinolin-4-yl)thio)propan-2-ol ( W14 ). White solid; yield: 37%; m.p. 155.1-155.4 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.25–8.21 (m, 2H, Ph-H), 8.13 (dd, J = 10.0 Hz, 1H, Ph-H), 8.04 (d, J = 7.3 Hz, 1H, Ph-H), 7.83–7.78 (m, 2H, Ph-H), 7.65–7.61 (m, 3H, Ph-H), 7.58 (d, J = 2.1 Hz, 1H, Ph-H), 7.55 (d, J = 8.8 Hz, 1H, Ph-H), 7.47 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.03 (dd, J = 10.0 Hz, 1H, Ph-H), 6.44 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.6 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.48 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.28 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.17–4.11 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.52 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.32 (dd, J = 5.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 154.08 (s), 148.08 (s), 146.78 (s), 137.45 (s), 134.75 (s), 131.44 (s), 130.51 (s), 130.01 (s), 129.32 (s), 129.20 (s), 128.91 (s), 126.82 (s), 125.06 (s), 123.76 (s), 123.26 (s), 120.91 (s), 119.63 (s), 113.47 (s), 111.71 (s), 100.54 (s), 68.38 (s), 51.37 (s), 35.43 (s); ESI-HRMS calcd for C 26 H 20 Cl 2 N 2 OS [M་H] ་ 479.07489, found 479.07462. 1-(5-chloro-1 H -indol-1-yl)-3-((2-(p-tolyl)quinolin-4-yl)thio)propan-2-ol ( W15 ). White solid; yield: 67%; m.p. 166.7-167.1 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.12–8.09 (m, 3H, Ph-H), 8.03 (d, J = 7.3 Hz, 1H, Ph-H), 7.80–7.76 (m, 2H, Ph-H), 7.62–7.59 (m, 1H, Ph-H), 7.59 (d, J = 2.1 Hz, 1H, Ph-H), 7.56 (d, J = 8.8 Hz, 1H, Ph-H), 7.47 (d, J = 3.1 Hz, 1H, Indol-2-H), 7.37 (d, J = 8.0 Hz, 2H, Ph-H), 7.03 (dd, J = 10.0 Hz, 1H, Ph-H), 6.44 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.73 (d, J = 5.6 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.49 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.29 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.19–4.11 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.51 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.31 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 2.41 (s, 3H,-Ph-CH 3 ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 155.30 (s), 147.54 (s), 146.92 (s), 139.49 (s), 135.90 (s), 134.76 (s), 131.43 (s), 130.31 (s), 129.91 (s), 129.51 (s), 129.32 (s), 127.35 (s), 126.41 (s), 124.94 (s), 123.77 (s), 123.22 (s), 120.94 (s), 119.64 (s), 113.47 (s), 111.71 (s), 100.53 (s), 68.38 (s), 51.40 (s), 35.44 (s), 21.06 (s); ESI-HRMS calcd for C 27 H 23 ClN 2 OS [M་H] ་ 459.12927, found 459.12924. 1-(5-methoxy-1 H -indol-1-yl)-3-((2-phenylquinolin-4-yl)thio)propan-2-ol ( W16 ). White solid; yield: 33%; m.p. 166.1-166.5 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.25–8.16 (m, 2H, Ph-H), 8.13 (dd, J = 5.0 Hz, 1H, Ph-H), 8.05 (d, J = 7.3 Hz, 1H, Ph-H), 7.86–7.74 (m, 2H, Ph-H), 7.67–7.57 (m, 1H, Ph-H), 7.63–7.52 (m, 2H, Ph-H),7.58–7.49 (m, 1H, Ph-H), 7.41 (d, J = 8.9 Hz, 1H, Indol-2-H), 7.35 (d, J = 3.0 Hz, 1H, Ph-H), 7.04 (d, J = 2.5 Hz, 1H, Ph-H), 6.66 (dd, J = 10.0 Hz, 1H, Ph-H), 6.35 (dd, J = 5.0 Hz, 1H, Indol-3-H), 5.71 (d, J = 5.6 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.44 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.24 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.18–4.11 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.72 (s, 3H, Indol-5-OCH 3 ), 3.50 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.30 (dd, J = 10.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 155.36 (s), 153.49 (s), 147.79 (s), 146.90 (s), 138.68 (s), 131.41 (s), 130.39 (s), 130.12 (s), 130.02 (s), 129.82 (s), 128.90 (s), 128.60 (s), 127.49 (s), 126.62 (s), 125.02 (s), 123.24 (s), 113.58 (s), 111.12 (s), 110.72 (s), 102.21 (s), 100.37 (s), 68.41 (s), 55.39 (s), 51.37 (s), 35.46 (s); ESI-HRMS calcd for C 27 H 24 N 2 O 2 S [M་H] ་ 441.16327, found 441.16313. 1-(5-methoxy-1 H -indol-1-yl)-3-((2-(m-tolyl)quinolin-4-yl)thio)propan-2-ol ( W17 ). White solid; yield: 29%; m.p. 142.8-143.2 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.13 (d, J = 8.4 Hz, 1H, Ph-H), 8.09 (s, 1H, Ph-H), 8.06 (d, J = 7.9 Hz, 1H, Ph-H), 7.97 (d, J = 8.0 Hz, 1H, Ph-H), 7.83(s, 1H, Ph-H), 7.81–7.77 (m, 1H, Ph-H), 7.64–7.60 (m, 1H, Ph-H), 7.46 (t, J = 7.6 Hz, 1H, Ph-H), 7.40 (d, J = 8.9 Hz, 1H, Indol-2-H), 7.34 (d, J = 3.2 Hz, 2H, Ph-H), 7.03 (d, J = 2.4 Hz, 1H, Ph-H), 6.64 (dd, J = 10.0 Hz, 1H, Ph-H), 6.34 (dd, J = 5.0 Hz, 1H, Indol-3-H), 5.71 (d, J = 5.7 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.45 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.23 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.18–4.10 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.71 (s, 3H, Indol-5-OCH 3 ), 3.50 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.31 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 2.46 (s, 3H,-Ph-CH 3 ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 155.51 (s), 153.48 (s), 147.66 (s), 146.91 (s), 138.69 (s), 138.10 (s), 131.41 (s), 130.46 (s), 130.36 (s), 130.11 (s), 129.99 (s), 128.81 (s), 128.60 (s), 128.00 (s), 126.57 (s), 125.04 (s), 124.72 (s), 123.26 (s), 113.79 (s), 111.08 (s), 110.69 (s), 102.20 (s), 100.34 (s), 68.40 (s), 55.37 (s), 51.34 (s), 35.47 (s), 21.33 (s); ESI-HRMS calcd for C 28 H 26 N 2 O 2 S [M་H] ་ 455.17889, found 455.17878. 1-(5-methoxy-1 H -indol-1-yl)-3-((2-(p-tolyl)quinolin-4-yl)thio)propan-2-ol ( W18 ). White solid; yield: 56%; m.p. 143.9-144.3 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.13–8.09 (m, 3H, Ph-H), 8.03 (d, J = 8.3 Hz, 1H, Ph-H), 7.80–7.75 (m, 2H, Ph-H), 7.62–7.58 (m, 1H, Ph-H), 7.41 (d, J = 8.8 Hz, 1H, Indol-2-H), 7.39–7.33 (m, 3H, Ph-H), 7.04 (d, J = 2.4 Hz, 1H, Ph-H), 6.67 (dd, J = 10.0 Hz, 1H, Ph-H), 6.35 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.71 (d, J = 5.6 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.44 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.24 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.17–4.11 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.72 (s, 3H, Indol-5-OCH 3 ), 3.47 (dd, J = 10.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.29 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 2.41 (s, 3H, -Ph-CH 3 ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 155.26 (s), 153.49 (s), 147.60 (s), 146.91 (s), 139.49 (s), 135.86 (s), 131.43 (s), 130.32 (s), 130.11 (s), 129.92 (s), 129.51 (s), 128.60 (s), 127.36 (s), 126.42 (s), 124.94 (s), 123.22 (s), 113.33 (s), 111.11 (s), 110.73 (s), 102.23 (s), 100.38 (s), 68.40 (s), 55.36 (s), 51.38 (s), 35.47 (s), 21.07 (s); ESI-HRMS calcd for C 28 H 26 N 2 O 2 S [M་H] ་ 455.17883, found 455.17878. 1-((2-(4-chlorophenyl)quinolin-4-yl)thio)-3-(5-methoxy-1 H -indol-1-yl)propan-2-ol ( W19 ). White solid; yield: 77%; m.p. 159.5-159.8 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.20 (d, J = 8.3 Hz, 2H, Ph-H), 8.12 (d, J = 8.4 Hz, 1H, Ph-H), 8.04 (d, J = 8.3 Hz, 1H, Ph-H), 7.85–7.74 (m, 2H, Ph-H), 7.62 (t, J = 8.4 Hz, 3H, Ph-H), 7.39 (d, J = 8.9 Hz, 1H, Ph-H), 7.34 (d, J = 3.0 Hz, 1H, Indol-2-H), 7.03 (d, J = 2.4 Hz, 1H, Ph-H), 6.65 (dd, J = 10.0 Hz, 1H, Ph-H), 6.35 (d, J = 3.0 Hz, 1H, Indol-3-H), 5.72 (d, J = 5.6 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.42 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.23 (dd, J = 10.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.16–4.09 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.72 (s, 3H, Indol-5-OCH 3 ), 3.51 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.29 (dd, J = 10.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 154.08 (s), 153.50 (s), 148.17 (s), 146.80 (s), 137.45 (s), 134.76 (s), 131.44 (s), 130.57 (s), 130.15 (s), 130.03 (s), 129.22 (s), 128.94 (s), 128.64 (s), 126.87 (s), 125.09 (s), 123.28 (s), 113.35 (s), 111.13 (s), 110.75 (s), 102.26 (s), 100.43 (s), 68.40 (s), 55.39 (s), 51.39 (s), 35.48 (s); ESI-HRMS calcd for C 27 H 23 ClN 2 O 2 S [M་H] ་ 475.12448, found 475.12415. 1-(5-methoxy-1 H -indol-1-yl)-3-((2-(3-methoxyphenyl)quinolin-4-yl)thio)propan-2-ol ( W20 ). White solid; yield: 63%; m.p. 167.1-167.4 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.13 (d, J = 8.2 Hz, 1H, Ph-H), 8.06 (d, J = 7.8 Hz, 1H, Ph-H), 7.85–7.82 (m, 2H, Ph-H), 7.81–7.78 (m, 1H, Ph-H), 7.77–7.74 (m, 1H, Ph-H), 7.64–7.60 (m, 1H, Ph-H), 7.49 (t, J = 7.9 Hz, 1H, Ph-H), 7.40 (d, J = 8.9 Hz, 1H, Indol-2-H), 7.34 (d, J = 3.1 Hz, 1H, Ph-H), 7.12 (dd, J = 10.0 Hz, 1H, Ph-H), 7.03 (d, J = 2.5 Hz, 1H, Ph-H), 6.65 (dd, J = 10.0 Hz, 1H, Ph-H), 6.34 (d, J = 3.1 Hz, 1H, Indol-3-H), 5.70 (d, J = 5.6 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.44 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.23 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.19–4.10 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.88 (s, 3H, -Ph-OCH 3 ), 3.71(s, 3H, Indol-5-OCH 3 ), 3.51 (dd, J = 10.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.34–3.29 (dd, J = 10.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 159.83 (s), 155.18 (s), 153.49 (s), 147.77 (s), 146.82 (s), 140.22 (s), 131.41 (s), 130.39 (s), 130.11 (s), 130.05 (s), 130.00 (s), 128.60 (s), 126.67 (s), 125.12 (s), 123.26 (s), 119.89 (s), 115.28 (s), 113.88 (s), 112.96 (s), 111.08 (s), 110.71 (s), 102.23 (s), 100.34 (s), 68.44 (s), 55.38 (s), 51.37 (s), 35.45 (s); ESI-HRMS calcd for C 28 H 26 N 2 O 3 S [M་H] ་ 471.17404, found 471.17369. 1-(5-methoxy-1 H -indol-1-yl)-3-((2-(4-(trifluoromethyl)phenyl)quinolin-4-yl)thio)propan-2-ol ( W21 ). White solid; yield: 69%; m.p. 152.9-153.3 ˚С; 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.36 (d, J = 8.0 Hz, 2H, Ph-H), 8.14 (dd, J = 5.0 Hz, 1H, Ph-H), 8.07 (d, J = 8.4 Hz, 1H, Ph-H), 7.91 (d, J = 8.2 Hz, 2H, Ph-H), 7.83–7.79 (m, 2H, Ph-H), 7.67–7.63 (m, 1H, Ph-H), 7.40 (d, J = 8.9 Hz, 1H, Indol-2-H), 7.35 (d, J = 3.0 Hz, 1H, Ph-H), 7.03 (d, J = 2.4 Hz, 1H, Ph-H), 6.65 (dd, J = 10.0 Hz, 1H, Ph-H), 6.35 (d, J = 3.5 Hz, 1H, Indol-3-H), 5.72 (d, J = 5.6 Hz, 1H, -CH 2 CH( OH )CH 2 -), 4.43 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.25 (dd, J = 15.0 Hz, 1H, - CH 2 CH(OH)CH 2 -), 4.19–4.11 (m, 1H, -CH 2 CH (OH)CH 2 -), 3.71(s, 3H, Indol-5-OCH 3 ), 3.49 (dd, J = 15.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ), 3.30 (dd, J = 10.0 Hz, 1H,-CH 2 CH(OH) CH 2 - ); 13 C NMR (125 MHz, DMSO- d 6 ) δ 153.78 (s), 153.49 (s), 148.46 (s), 146.77 (s), 142.49 (s), 131.44 (s), 130.65 (s), 130.14 (s), 129.5 (dd, 1 J C−F = 252.0 Hz), 128.63 (s), 128.20 (s), 127.18 (s), 125.7 (dd, 3 J C−F = 7.5 Hz), 125.50 (s), 125.26 (s), 123.29 (s), 113.69 (s), 111.10 (s), 110.73 (s), 102.23 (s), 100.43 (s), 68.40 (s), 55.33 (s), 51.38 (s), 35.51 (s); ESI-HRMS calcd for C 28 H 23 F 3 N 2 O 2 S [M་H] ་ 509.15109, found 509.15051. 4.3 Anti-TMV activity assay 4.3.1 Curative activity Silicon carbide was evenly applied to both sides of the tobacco leaf, and then TMV (500 µ g/mL) was brushed vigorously and evenly onto both sides of the leaf with a brush. After 0.5 h of virus infection, the Silicon carbide was rinsed off, and after the leaves were dried, the tips of the heart-leaf tobacco were turned toward themselves, and the left half of the tobacco was used as a blank control, and 500 µ g/mL of the target compounds were brushed evenly onto the right half of the tobacco, and the right half of the tobacco was transferred to an environment at 28°C for 2–3 d. The number of spots on the left and right sides of tobacco was recorded, and then the inhibition rate was calculated by the formula of inhibition rate. 4.3.2 Protective activity The leaf tips of the heartleaf tobacco were turned toward themselves, and the left half of the tobacco leaf was used as a blank control. A solution of the compound (500 µ g/mL) was applied to the right side of the tobacco leaf using a brush. After 20–24 h, carborundum was evenly applied to both sides of the tobacco leaf, and then TMV (500 µ g/mL) was applied to both sides of the tobacco leaf. After 0.5 h of virus infection, the silicon carbide was washed off. After completion, the tobacco leaves were transferred to a temperature of 28°C for 2–3 d. The number of spots on the left and right sides of the tobacco leaves was recorded and the inhibition rate was calculated using the formula for inhibition rate. 4.3.3 Inactivation activity Equal volumes of 1000 µ g/mL of the target compound to be tested and 1000 µ g/mL of TMV were mixed homogeneously as passivated 500 µ g/mL TMV and left for 0.5 h. The left half of the tobacco leaf was used as a blank control, and the left side of the tobacco leaf was dipped into 500 µ g/mL TMV virus with a row pen, and the right side of the tobacco leaf was uniformly brushed with 500 µ g/mL of TMV that had been passivated for 0.5 h. The carbons were washed off after infection for 0.5 h. The left half of the tobacco leaf was used as a blank control, and the left half of the tobacco leaf was used as a blank control. At the end, the tobacco was transferred to a temperature of 28°C for 2–3 d. The number of spots on the left and right sides of the tobacco was recorded and the inhibition rate was calculated using the formula for inhibition rate. 4.4 Inhibition rate NNM was utilized as a drug control, while the left side of the tobacco leaf served as a blank control. After counting the number of spots on the left and right tobacco leaves, the following formula was used to determine the anti-TMV inhibition rate: Inhibition rate = [(L–R)/L] × 100% L: the number of spots on the left half-leaf; R: the number of spots on the right half-leaf. 4.5 Microscale thermophoresis analysis Using the formula [m (mg) = M (relative molecular mass) × 4/1000], the target chemical was weighed and dissolved in 100 µ L DMSO. To prepare the mother liquor, 10 µ L of DMSO dissolved solution was added to a 200 µ L centrifuge tube, followed by 190 µ L of phosphate buffer saline. The 16 centrifuge tubes were numbered 1–16. 10 µ L of mother liquor was added to No. 1 and No. 2 tubes, and 10 µ L of PBS to No. 2–16 tubes. The mother liquor in No. 2 centrifuge tube was mixed with PBS. The mixed drug solution in 10 µ L No. 2 centrifuge tube was transferred to No. 3 centrifuge tube. Mix the solution in No. 3 centrifuge tube, then transfer 10 µ L to No. 4 centrifuge tube. Repeat till No.16 centrifuge tube. Finally, 10 µ L of the combined drug solution was removed from the No. 16 centrifuge tube and discarded. To test MST, 10 µ L of labeled TMV-CP-labeled protein was introduced to the 1–16 labeled drug combination. The mixture was then filled with a customized capillary. Each capillary was measured sequentially. 4.6 Single‑crystal X‑ray diffraction experiments The single crystal X-ray diffraction experiment is to select the crystal with neat appearance and no impurities from W14 for single crystal diffraction experiment. The crystal was placed on a single crystal X-ray diffractometer, and the diffraction data were measured and collected at 273 K using MoKα. According to the collected data, the molecular structure was further determined by structural analysis. Analysis of crystal structure with Olex-2.0 software. In addition, the crystal structure and crystal stacking diagram were obtained by Mercury software. 4.7 Molecular docking The 2D structures of the target compounds W20 and NNM were first drawn using Chemdraw. Then the 2D structure of W20 was converted to 3D structure using Chemdraw 3D. Next, the 3D structure of TMV-CP was downloaded from the PDB database. In addition, TMV-CP was processed in Discovery Studio software to remove water molecules and small molecule ligand structures. Docking and landscaping were performed in with PyMOL. 4.8 Determination of MDA content The content of malondialdehyde (MDA) in tobacco leaves infected with TMV treated with compound W20 was tested by literature method. First, select 15–20 leaves with good growth and the same leaf size, prune the old leaves and the small leaves at the top, and leave 4–6 leaves. Dip the medicinal liquid with the concentration of 500 µ g/mL with a brush, and smear it evenly on the selected tobacco leaves. The negative control group (DMSO solution) will do the same operation. After 24 h, the TMV virus will be inoculated, and then the 1, 3, 5 and 7 d will be collected respectively. They were divided into CK, CK + TMV, W20 and W20 + TMV groups, and then the absorbance of each sample at 532 and 600 nm was determined according to the method in the kit instructions. The calculation formula of malondialdehyde content was referred to the kit instructions. Declarations Supporting information The supporting information includes NMR and HRMS spectrogram data of the target compound and detailed crystal data of W14 . Conflicts of interest The authors declare that there are no competing financial interests. Author Contribution Wei Xue，Zhenchao Wang: conceived and designed the experiments. Provide experiment drawing software and method. Bangcan He: performed the experiments, analyzed the data and writing-original draft preparation. Yuzhi Hu, Yishan Qing: evaluated the Antiviral activity of the target compounds. Yufang Zhang, Xingping Luo: provided the material for evaluating the Antiviral activity. All authors have given approval to the final version of the manuscript. Acknowledgement The authors gratefully acknowledge the National Nature Science Foundation of China (22007022), the Science Foundation of Guizhou Province (No. 20192452). References Wang PY, Zhou L, Zhou J, Wu ZB, Xue W, Song BA, Yang S (2016) Synthesis and antibacterial activity of pyridinium-tailored 2,5-substituted-1,3,4-oxadiazole thioether/sulfoxide/sulfone derivatives. 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compounds\u003c/p\u003e","description":"","filename":"F3.png","url":"https://assets-eu.researchsquare.com/files/rs-3964276/v1/224637bcecd11db69975edd8.png"},{"id":51450037,"identity":"5782d51f-9b66-4a30-97ac-5ed2c1e36615","added_by":"auto","created_at":"2024-02-21 20:16:47","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":107287,"visible":true,"origin":"","legend":"\u003cp\u003eCrystal structure (\u003cstrong\u003eA\u003c/strong\u003e) and crystal packing diagram (\u003cstrong\u003eB\u003c/strong\u003e) of \u003cstrong\u003eW14\u003c/strong\u003e\u003c/p\u003e","description":"","filename":"F4.png","url":"https://assets-eu.researchsquare.com/files/rs-3964276/v1/7c64db86e75c5f6f7654f50c.png"},{"id":51450039,"identity":"c947a6f4-7dd6-4766-9012-95628b0acccb","added_by":"auto","created_at":"2024-02-21 20:16:47","extension":"png","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":126173,"visible":true,"origin":"","legend":"\u003cp\u003eAgainst TMV activities of \u003cstrong\u003eW20\u003c/strong\u003e and ningnanmycin \u003cem\u003ein vivo\u003c/em\u003e\u003c/p\u003e","description":"","filename":"F5.png","url":"https://assets-eu.researchsquare.com/files/rs-3964276/v1/0e8a217e6c46d7e69ec0884f.png"},{"id":51450041,"identity":"cb6fe36f-48bc-4e94-ab23-e7402320439e","added_by":"auto","created_at":"2024-02-21 20:16:48","extension":"png","order_by":6,"title":"Figure 6","display":"","copyAsset":false,"role":"figure","size":25485,"visible":true,"origin":"","legend":"\u003cp\u003eMicroscale thermophoresis results of compounds \u003cstrong\u003eW18\u003c/strong\u003e, \u003cstrong\u003eW20\u003c/strong\u003e and ningnamycin\u003c/p\u003e","description":"","filename":"F6.png","url":"https://assets-eu.researchsquare.com/files/rs-3964276/v1/1f4d2916ff3de5525a22361f.png"},{"id":51450040,"identity":"45db67ae-5ca9-45c1-a109-82b3b59f196a","added_by":"auto","created_at":"2024-02-21 20:16:47","extension":"png","order_by":7,"title":"Figure 7","display":"","copyAsset":false,"role":"figure","size":161000,"visible":true,"origin":"","legend":"\u003cp\u003eMolecular docking diagram of ningnanmycin (\u003cstrong\u003eA\u003c/strong\u003e, \u003cstrong\u003eB\u003c/strong\u003e, \u003cstrong\u003eC\u003c/strong\u003e) and \u003cstrong\u003eW20\u003c/strong\u003e (\u003cstrong\u003eD\u003c/strong\u003e, \u003cstrong\u003eE\u003c/strong\u003e, \u003cstrong\u003eF\u003c/strong\u003e) with tobacco Mosaic virus coat protein (TMV-CP)\u003c/p\u003e","description":"","filename":"F7.png","url":"https://assets-eu.researchsquare.com/files/rs-3964276/v1/0cf680735194d8f643db94d4.png"},{"id":51450279,"identity":"0e5b246c-60ad-4865-908c-83de3c42222f","added_by":"auto","created_at":"2024-02-21 20:24:48","extension":"png","order_by":8,"title":"Figure 8","display":"","copyAsset":false,"role":"figure","size":33092,"visible":true,"origin":"","legend":"\u003cp\u003eEffects of \u003cstrong\u003eW20\u003c/strong\u003e on MDA content in tobacco\u003c/p\u003e","description":"","filename":"F8.png","url":"https://assets-eu.researchsquare.com/files/rs-3964276/v1/9bdc8de461bcb4a1731dc5b2.png"},{"id":61596402,"identity":"8b4c20b2-b706-474e-a944-6ba59dd6f000","added_by":"auto","created_at":"2024-08-01 17:27:08","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":2040547,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-3964276/v1/0b097d8d-ce1c-4711-acf1-d65152ce9e09.pdf"},{"id":51450035,"identity":"f74db590-566a-46cc-b583-cc0948049208","added_by":"auto","created_at":"2024-02-21 20:16:47","extension":"png","order_by":2,"title":"","display":"","copyAsset":false,"role":"supplement","size":19500,"visible":true,"origin":"","legend":"","description":"","filename":"Scheme1.png","url":"https://assets-eu.researchsquare.com/files/rs-3964276/v1/43d02c2565a4d933b6027de2.png"},{"id":51450043,"identity":"1d73a63f-7b5b-4bba-8c39-fd276f186886","added_by":"auto","created_at":"2024-02-21 20:16:48","extension":"jpg","order_by":3,"title":"","display":"","copyAsset":false,"role":"supplement","size":167737,"visible":true,"origin":"","legend":"","description":"","filename":"GA.jpg","url":"https://assets-eu.researchsquare.com/files/rs-3964276/v1/05ddcd4acf6eb9ab6f0e3614.jpg"},{"id":51450044,"identity":"1351d813-053e-4aad-bc0e-5f50df4b31b3","added_by":"auto","created_at":"2024-02-21 20:16:48","extension":"docx","order_by":4,"title":"","display":"","copyAsset":false,"role":"supplement","size":5628527,"visible":true,"origin":"","legend":"","description":"","filename":"Supportinformation.docx.docx","url":"https://assets-eu.researchsquare.com/files/rs-3964276/v1/305abb2df6ffb16cd92c721f.docx"}],"financialInterests":"No competing interests reported.","formattedTitle":"Design, Synthesis and Antiviral Activity of Indole Derivatives Containing Quinoline Moiety","fulltext":[{"header":"1 Introduction","content":"\u003cp\u003eTobacco mosaic virus (TMV) can infect tobacco, tomato, pepper and other crops [\u003cspan additionalcitationids=\"CR2 CR3\" citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e4\u003c/span\u003e]. Once infected, the plant was difficult to cure and severely affects the quality and yield of tobacco [\u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e]. It was one of the most studied viruses in the world [\u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e6\u003c/span\u003e]. The long-term use of traditional antiviral drugs such as NNM and ribavirin had led to varying degrees of resistance to plant viruses [\u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e, \u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e8\u003c/span\u003e]. It had caused serious problems such as environmental pollution, increased resistance, and pesticide residues [\u003cspan additionalcitationids=\"CR10\" citationid=\"CR9\" class=\"CitationRef\"\u003e9\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e11\u003c/span\u003e]. Therefore, new types of pesticides are the trend, and it was important to develop high efficiency, low toxicity, easy degradation, environmentally friendly and wide range of biological activity pesticides.\u003c/p\u003e \u003cp\u003eIndole (Fig.\u0026nbsp;\u003cspan refid=\"Fig1\" class=\"InternalRef\"\u003e1\u003c/span\u003e) was a nitrogen-containing benzopyrrole alkaloid found not only in natural plants such as chimonanthus praecox, oleander, jasmine, croton root, citrus and orange blossoms [\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e, \u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e], but also in many animals and marine organisms [\u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e14\u003c/span\u003e]. With the progress of science and technology and the development of human life sciences, a series of indole derivatives had been synthesized by structural modification using indole as a starting point. Subsequent studies had revealed that indole derivatives had remarkable biological activities, and their derivatives had attracted attention for their good antibacterial [\u003cspan additionalcitationids=\"CR16\" citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR17\" class=\"CitationRef\"\u003e17\u003c/span\u003e], antiviral [\u003cspan additionalcitationids=\"CR19 CR20\" citationid=\"CR18\" class=\"CitationRef\"\u003e18\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR21\" class=\"CitationRef\"\u003e21\u003c/span\u003e], antioxidant [\u003cspan citationid=\"CR22\" class=\"CitationRef\"\u003e22\u003c/span\u003e], anti-inflammatory [\u003cspan citationid=\"CR23\" class=\"CitationRef\"\u003e23\u003c/span\u003e], anticancer [\u003cspan citationid=\"CR24\" class=\"CitationRef\"\u003e24\u003c/span\u003e], antitumor [\u003cspan citationid=\"CR25\" class=\"CitationRef\"\u003e25\u003c/span\u003e], protein kinase inhibitory properties [\u003cspan citationid=\"CR26\" class=\"CitationRef\"\u003e26\u003c/span\u003e] and these derivatives had been widely used in pesticides, pharmaceuticals, dyestuffs, and fragrances, among other industries.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eQuinolines [\u003cspan citationid=\"CR27\" class=\"CitationRef\"\u003e27\u003c/span\u003e] (Fig.\u0026nbsp;\u003cspan refid=\"Fig1\" class=\"InternalRef\"\u003e1\u003c/span\u003e), also known as benzopyridines, had a bicyclic structure and are \u003cem\u003eN\u003c/em\u003e-heterocyclic aromatic compounds. Quinolines and isoquinolines obtained from natural products, this class of compounds had attracted much attention from researchers due to its simple chemical structure and remarkable biological activity [\u003cspan citationid=\"CR28\" class=\"CitationRef\"\u003e28\u003c/span\u003e]. Quinoline was a naturally active alkaloid [\u003cspan citationid=\"CR29\" class=\"CitationRef\"\u003e29\u003c/span\u003e]. It had received wide attention due to its favorable antibacterial [\u003cspan citationid=\"CR30\" class=\"CitationRef\"\u003e30\u003c/span\u003e, \u003cspan citationid=\"CR31\" class=\"CitationRef\"\u003e31\u003c/span\u003e], antitubercular [\u003cspan citationid=\"CR32\" class=\"CitationRef\"\u003e32\u003c/span\u003e], anticancer [\u003cspan citationid=\"CR33\" class=\"CitationRef\"\u003e33\u003c/span\u003e] and other biological activities. In which Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003e shows a commercial medicament containing quinoline.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eTherefore, a series of indole derivatives containing quinoline were designed and synthesized by active splicing principle in this study. The design idea of the target compounds was shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig3\" class=\"InternalRef\"\u003e3\u003c/span\u003e Preliminary bioactivity tests showed that some of the compounds possessed good antiviral activity. Among them, \u003cb\u003eW20\u003c/b\u003e showed significant inhibitory activity against TMV. Meanwhile, MST and molecular docking indicated that the compound for \u003cb\u003eW20\u003c/b\u003e had strong binding ability against TMV CP.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eFigure\u0026nbsp;\u003cspan refid=\"Fig1\" class=\"InternalRef\"\u003e1\u003c/span\u003e\u003c/p\u003e \u003cp\u003eFigure\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003e\u003c/p\u003e \u003cp\u003eFigure\u0026nbsp;\u003cspan refid=\"Fig3\" class=\"InternalRef\"\u003e3\u003c/span\u003e\u003c/p\u003e"},{"header":"2 Results and discussion","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003e2.1 Chemistry\u003c/h2\u003e \u003cp\u003eScheme \u003cspan refid=\"Sch1\" class=\"InternalRef\"\u003e1\u003c/span\u003e\u003c/p\u003e \u003cp\u003eThe synthesis of the target compounds was carried out as shown in Scheme \u003cspan refid=\"Sch1\" class=\"InternalRef\"\u003e1\u003c/span\u003e and the synthesized compounds were characterized by NMR and HRMS. Intermediate \u003cb\u003e1\u003c/b\u003e was obtained by reacting various substituted benzoyl chloride with o-aminoacetophenone. Secondly, intermediate \u003cb\u003e1\u003c/b\u003e was dissolved in 1,4-dioxane and reacted with sodium hydroxide as acid-binding agent to produce intermediate \u003cb\u003e2\u003c/b\u003e by refluxing at 110 ℃, and then intermediate \u003cb\u003e2\u003c/b\u003e was reacted with diphosphorus pentasulfide to obtain intermediate \u003cb\u003e3\u003c/b\u003e. Further, intermediate \u003cb\u003e4\u003c/b\u003e was obtained by using substituting indole as a raw material and refluxing with bromopropylene oxide under alkaline condition by heating at 45 ℃ for 12 h. Finally, K\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e and 20 mL of DMF were added to a round bottom flask along with Intermediate \u003cb\u003e4\u003c/b\u003e and after 0.5 h, Intermediate \u003cb\u003e3\u003c/b\u003e was added to the reaction mixture. The reaction was followed by TLC at 77\u0026deg;C for about 10 h. It was then mixed with 90 mL of distilled water and extracted with ethyl acetate. The lower liquid phase was recovered, dried, filtered and washed three times with saturated brine to remove the ethyl acetate solvent. Finally, \u003cb\u003eW1-W21\u003c/b\u003e was purified by column chromatography (petroleum ether: ethyl acetate\u0026thinsp;=\u0026thinsp;15:1, \u003cem\u003ev/v\u003c/em\u003e).\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec4\" class=\"Section2\"\u003e \u003ch2\u003e2.2 Spectral characteristic of title compounds\u003c/h2\u003e \u003cp\u003e \u003cb\u003eW1-W21\u003c/b\u003e was confirmed on NMR and HRMS spectra. Take \u003cb\u003eW3\u003c/b\u003e as an example: In the \u003csup\u003e1\u003c/sup\u003eH NMR spectrum, the double peak at \u003cem\u003eδ\u003c/em\u003e 7.36 was attributed to the existence of H in the 2-position of indole ring. The double peak at \u003cem\u003eδ\u003c/em\u003e 6.40 was attributed to the existence of H in the 3-position of indole ring. And the double peak at \u003cem\u003eδ\u003c/em\u003e 5.69 was attributed to the existence of -OH in the aliphatic chain. The two high frequency quadruple peaks of \u003cem\u003eδ\u003c/em\u003e 4.46 and \u003cem\u003eδ\u003c/em\u003e 4.25 are attributed to the existence of aliphatic chain (-\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-) connected with indole ring. The multiple peaks of \u003cem\u003eδ\u003c/em\u003e 4.20\u0026ndash;4.13 are attributed to the existence of aliphatic chain (-CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-) connected with indole ring. The two high frequency quadruple peaks of \u003cem\u003eδ\u003c/em\u003e 3.44 and \u003cem\u003eδ\u003c/em\u003e 3.23 are attributed to the existence of aliphatic chain (-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e) linked to indole ring. In \u003csup\u003e13\u003c/sup\u003eC NMR spectrum, \u003cem\u003eδ\u003c/em\u003e 127.49 was attributed to the existence of C in position 2 of indole ring. And \u003cem\u003eδ\u003c/em\u003e 101.08 was attributed to the existence of C in position 3 of indole ring. The three signal peaks at \u003cem\u003eδ\u003c/em\u003e 51.49 and \u003cem\u003eδ\u003c/em\u003e 35.90 were attributed to the existence of C on the aliphatic chain (-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-) linked to the indole ring. The obvious single-line peak at \u003cem\u003eδ\u003c/em\u003e -116.46 in \u003csup\u003e19\u003c/sup\u003eF NMR spectrum confirmed the existence of F in benzene ring of indole structure. In the HRMS spectrogram, the target product's HRMS [M\u0026thinsp;+\u0026thinsp;H]\u003csup\u003e+\u003c/sup\u003e Calcd for C\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eFN\u003csub\u003e2\u003c/sub\u003eOS 429.14313, found 429.14314. The measured value and theoretical calculation value (m/z 0.0030) are within the error range, and the structure of the target compound \u003cb\u003eW20\u003c/b\u003e was further confirmed. Detailed data are included in the \u003cb\u003eSupporting Information\u003c/b\u003e. In addition, in order to further determine the structure of the target compound, \u003cb\u003eW14\u003c/b\u003e was analyzed by single crystal X-ray diffraction, and further determined the structure of indole derivatives containing quinoline. The crystal structure (Fig.\u0026nbsp;\u003cspan refid=\"Fig4\" class=\"InternalRef\"\u003e4\u003c/span\u003e) and data (CCDC: 2269080) can be obtained by accessing the Cambridge Crystal Database. More characterization data are provided in the \u003cb\u003eSupporting Information\u003c/b\u003e.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eFigure\u0026nbsp;\u003cspan refid=\"Fig4\" class=\"InternalRef\"\u003e4\u003c/span\u003e\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec5\" class=\"Section2\"\u003e \u003ch2\u003e2.3 Antiviral activity\u003c/h2\u003e \u003cp\u003eHalf-leaf spot method was employed to investigate the antiviral activity of target compounds on Nicotiana tabacum leaves grown at the same age and TMV (500 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL) [\u003cspan additionalcitationids=\"CR35 CR36\" citationid=\"CR34\" class=\"CitationRef\"\u003e34\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR37\" class=\"CitationRef\"\u003e37\u003c/span\u003e]. The results are shown in Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e and Fig.\u0026nbsp;\u003cspan refid=\"Fig5\" class=\"InternalRef\"\u003e5\u003c/span\u003e that the concentration was 500 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL, the inhibition rates of \u003cb\u003eW7\u003c/b\u003e, \u003cb\u003eW16\u003c/b\u003e, \u003cb\u003eW18\u003c/b\u003e, \u003cb\u003eW20\u003c/b\u003e and \u003cb\u003eW21\u003c/b\u003e were 75.2, 64.5, 68.4, 75.1 and 65.9%, respectively, in terms of curative activity, which were superior to the control agent NNM (61.3%). The inhibition rates of compounds \u003cb\u003eW7\u003c/b\u003e, \u003cb\u003eW8\u003c/b\u003e, \u003cb\u003eW16\u003c/b\u003e, \u003cb\u003eW17\u003c/b\u003e, \u003cb\u003eW18\u003c/b\u003e, \u003cb\u003eW20\u003c/b\u003e and \u003cb\u003eW21\u003c/b\u003e were 79.9, 68.3, 66.5, 71.8, 75.3, 82.7 and 67.3%, respectively, in terms of protective activity, which were better than the control agent NNM (66.0%). When it came to inactivation activity, the inhibition rates of \u003cb\u003eW7\u003c/b\u003e, \u003cb\u003eW18\u003c/b\u003e and \u003cb\u003eW20\u003c/b\u003e were 68.1, 67.9 and 71.7%, which were close to the control agent NNM (82.2%).\u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab1\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 1\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eAntiviral activities of the target compounds against TMV at 500 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL \u003cem\u003ein vivo\u003c/em\u003e \u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"6\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\"\u0026plusmn;\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\"\u0026plusmn;\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\"\u0026plusmn;\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eCompd.\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eR\u003csub\u003e1\u003c/sub\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eR\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCurative\u003c/p\u003e \u003cp\u003eactivity (%)\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eProtection\u003c/p\u003e \u003cp\u003eactivity (%)\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\"\u003e \u003cp\u003eInactivation\u003c/p\u003e \u003cp\u003eactivity (%)\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e2-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e53.8\u0026thinsp;\u0026plusmn;\u0026thinsp;2.9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e54.6\u0026thinsp;\u0026plusmn;\u0026thinsp;4.1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e46.3\u0026thinsp;\u0026plusmn;\u0026thinsp;3.5\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW2\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e53.8\u0026thinsp;\u0026plusmn;\u0026thinsp;2.7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e59.9\u0026thinsp;\u0026plusmn;\u0026thinsp;2.8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e50.9\u0026thinsp;\u0026plusmn;\u0026thinsp;3.7\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW3\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e2-F\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e46.4\u0026thinsp;\u0026plusmn;\u0026thinsp;4.8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e52.9\u0026thinsp;\u0026plusmn;\u0026thinsp;4.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e45.9\u0026thinsp;\u0026plusmn;\u0026thinsp;2.9\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW4\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e3-CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e52.7\u0026thinsp;\u0026plusmn;\u0026thinsp;1.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e55.1\u0026thinsp;\u0026plusmn;\u0026thinsp;6.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e50.3\u0026thinsp;\u0026plusmn;\u0026thinsp;2.5\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW5\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4-CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e49.1\u0026thinsp;\u0026plusmn;\u0026thinsp;3.3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e64.0\u0026thinsp;\u0026plusmn;\u0026thinsp;2.7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e45.2\u0026thinsp;\u0026plusmn;\u0026thinsp;3.2\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW6\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e3-OCH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e51.6\u0026thinsp;\u0026plusmn;\u0026thinsp;2.0\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e59.3\u0026thinsp;\u0026plusmn;\u0026thinsp;1.1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e53.4\u0026thinsp;\u0026plusmn;\u0026thinsp;1.3\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW7\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-Br\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e75.2\u0026thinsp;\u0026plusmn;\u0026thinsp;3.8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e79.9\u0026thinsp;\u0026plusmn;\u0026thinsp;1.3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e68.1\u0026thinsp;\u0026plusmn;\u0026thinsp;4.5\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW8\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-Br\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e2-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e62.1\u0026thinsp;\u0026plusmn;\u0026thinsp;3.5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e68.3\u0026thinsp;\u0026plusmn;\u0026thinsp;2.0\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e47.5\u0026thinsp;\u0026plusmn;\u0026thinsp;4.5\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW9\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-Br\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e46.1\u0026thinsp;\u0026plusmn;\u0026thinsp;2.0\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e51.2\u0026thinsp;\u0026plusmn;\u0026thinsp;3.5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e39.6\u0026thinsp;\u0026plusmn;\u0026thinsp;4.1\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW10\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-Br\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4-CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e50.8\u0026thinsp;\u0026plusmn;\u0026thinsp;4.9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e61.1\u0026thinsp;\u0026plusmn;\u0026thinsp;1.3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e48.5\u0026thinsp;\u0026plusmn;\u0026thinsp;4.0\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW11\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e42.0\u0026thinsp;\u0026plusmn;\u0026thinsp;1.9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e61.0\u0026thinsp;\u0026plusmn;\u0026thinsp;4.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e51.0\u0026thinsp;\u0026plusmn;\u0026thinsp;0.7\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW12\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4-CF\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e59.1\u0026thinsp;\u0026plusmn;\u0026thinsp;5.0\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e63.4\u0026thinsp;\u0026plusmn;\u0026thinsp;2.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e57.2\u0026thinsp;\u0026plusmn;\u0026thinsp;5.0\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW13\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e2,4-di-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e51.7\u0026thinsp;\u0026plusmn;\u0026thinsp;5.7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e53.0\u0026thinsp;\u0026plusmn;\u0026thinsp;4.8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e45.1\u0026thinsp;\u0026plusmn;\u0026thinsp;4.7\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW14\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e40.8\u0026thinsp;\u0026plusmn;\u0026thinsp;2.6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e47.3\u0026thinsp;\u0026plusmn;\u0026thinsp;4.5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e38.7\u0026thinsp;\u0026plusmn;\u0026thinsp;4.1\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW15\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4-CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e54.6\u0026thinsp;\u0026plusmn;\u0026thinsp;4.5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e61.1\u0026thinsp;\u0026plusmn;\u0026thinsp;1.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e48.2\u0026thinsp;\u0026plusmn;\u0026thinsp;1.8\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW16\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-OCH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e64.5\u0026thinsp;\u0026plusmn;\u0026thinsp;2.8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e66.5\u0026thinsp;\u0026plusmn;\u0026thinsp;2.1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e56.1\u0026thinsp;\u0026plusmn;\u0026thinsp;2.9\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW17\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-OCH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e3-CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e58.6\u0026thinsp;\u0026plusmn;\u0026thinsp;2.8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e71.8\u0026thinsp;\u0026plusmn;\u0026thinsp;2.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e55.0\u0026thinsp;\u0026plusmn;\u0026thinsp;3.2\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW18\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-OCH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4-CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e68.4\u0026thinsp;\u0026plusmn;\u0026thinsp;3.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e75.3\u0026thinsp;\u0026plusmn;\u0026thinsp;1.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e67.9\u0026thinsp;\u0026plusmn;\u0026thinsp;1.6\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW19\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-OCH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e56.4\u0026thinsp;\u0026plusmn;\u0026thinsp;3.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e61.5\u0026thinsp;\u0026plusmn;\u0026thinsp;2.5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e52.5\u0026thinsp;\u0026plusmn;\u0026thinsp;4.6\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW20\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-OCH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e3-OCH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e75.1\u0026thinsp;\u0026plusmn;\u0026thinsp;3.5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e82.7\u0026thinsp;\u0026plusmn;\u0026thinsp;0.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e71.7\u0026thinsp;\u0026plusmn;\u0026thinsp;6.6\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW21\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e5-OCH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4-CF\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e65.9\u0026thinsp;\u0026plusmn;\u0026thinsp;2.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e67.3\u0026thinsp;\u0026plusmn;\u0026thinsp;2.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e56.1\u0026thinsp;\u0026plusmn;\u0026thinsp;4.7\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eningnanmycin\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c4\"\u003e \u003cp\u003e61.3\u0026thinsp;\u0026plusmn;\u0026thinsp;4.3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c5\"\u003e \u003cp\u003e66.0\u0026thinsp;\u0026plusmn;\u0026thinsp;3.1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c6\"\u003e \u003cp\u003e82.2\u0026thinsp;\u0026plusmn;\u0026thinsp;0.8\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003ctfoot\u003e \u003ctr\u003e\u003ctd colspan=\"6\"\u003e\u003csup\u003ea\u003c/sup\u003e Average values of three replicates. \u003csup\u003eb\u003c/sup\u003e The commercial antiviral agents ningnanmycin.\u003c/td\u003e\u003c/tr\u003e \u003c/tfoot\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eTo further confirm the antiviral activity of our target compounds, the EC\u003csub\u003e50\u003c/sub\u003e value were tested for some compounds (Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e). The results show that the EC\u003csub\u003e50\u003c/sub\u003e value of \u003cb\u003eW7\u003c/b\u003e, \u003cb\u003eW18\u003c/b\u003e, \u003cb\u003eW20\u003c/b\u003e and \u003cb\u003eW21\u003c/b\u003e were 86.6, 137.3, 84.4 and 168.4 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL, respectively, in terms of curative activity, which were superior to the control agent NNM (205.1 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL). The EC\u003csub\u003e50\u003c/sub\u003e value of \u003cb\u003eW7\u003c/b\u003e, \u003cb\u003eW8\u003c/b\u003e, \u003cb\u003eW16\u003c/b\u003e, \u003cb\u003eW17\u003c/b\u003e, \u003cb\u003eW18\u003c/b\u003e, \u003cb\u003eW20\u003c/b\u003e and \u003cb\u003eW21\u003c/b\u003e were 76.8, 119.9, 162.7, 101.4, 96.3, 65.7 and 119.6 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL, respectively, in terms of protective activity, which were better than NNM (162.0 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL).\u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab2\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 2\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eThe EC\u003csub\u003e50\u003c/sub\u003e values of several target compounds against TMV\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"5\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eCompd.\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eRegression equation\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003er\u003csup\u003e2\u003c/sup\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eEC\u003csub\u003e50\u003c/sub\u003e (\u0026micro;g/mL)\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eCurative activity\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003eW7\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ey\u0026thinsp;=\u0026thinsp;0.6920x\u0026thinsp;+\u0026thinsp;3.6591\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.9964\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e86.6\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003eW18\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ey\u0026thinsp;=\u0026thinsp;0.8773x\u0026thinsp;+\u0026thinsp;3.1245\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.9919\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e137.3\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003eW20\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ey\u0026thinsp;=\u0026thinsp;0.7619x\u0026thinsp;+\u0026thinsp;3.5323\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.9864\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e84.4\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003eW21\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ey\u0026thinsp;=\u0026thinsp;0.7720x\u0026thinsp;+\u0026thinsp;3.2813\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.9810\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e168.4\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eningnanmycin\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ey\u0026thinsp;=\u0026thinsp;0.8089x\u0026thinsp;+\u0026thinsp;3.1299\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.9943\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e205.1\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eProtection activity\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003eW7\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ey\u0026thinsp;=\u0026thinsp;0.7983x\u0026thinsp;+\u0026thinsp;3.4947\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.9961\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e76.8\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003eW8\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ey\u0026thinsp;=\u0026thinsp;0.6218x\u0026thinsp;+\u0026thinsp;3.7073\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.9722\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e119.9\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003eW16\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ey\u0026thinsp;=\u0026thinsp;0.7487x\u0026thinsp;+\u0026thinsp;3.3443\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.9996\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e162.7\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003eW17\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ey\u0026thinsp;=\u0026thinsp;0.8257x\u0026thinsp;+\u0026thinsp;3.3437\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.9943\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e101.4\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003eW18\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ey\u0026thinsp;=\u0026thinsp;0.7548x\u0026thinsp;+\u0026thinsp;3.5028\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.9970\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e96.3\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003eW20\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ey\u0026thinsp;=\u0026thinsp;0.8500x\u0026thinsp;+\u0026thinsp;3.4548\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.9824\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e65.7\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003eW21\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ey\u0026thinsp;=\u0026thinsp;0.6546x\u0026thinsp;+\u0026thinsp;3.6398\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.9846\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e119.6\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eningnanmycin\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ey\u0026thinsp;=\u0026thinsp;0.5410x\u0026thinsp;+\u0026thinsp;3.8046\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.9908\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e162.0\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003ctfoot\u003e \u003ctr\u003e\u003ctd colspan=\"5\"\u003e\u003csup\u003ea\u003c/sup\u003e Average values of three replicates. \u003csup\u003eb\u003c/sup\u003e The commercial antiviral agents ningnanmycin.\u003c/td\u003e\u003c/tr\u003e \u003c/tfoot\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003eTable\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e\u003c/p\u003e \u003cp\u003eFigure\u0026nbsp;\u003cspan refid=\"Fig5\" class=\"InternalRef\"\u003e5\u003c/span\u003e\u003c/p\u003e \u003cp\u003eTable\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec6\" class=\"Section2\"\u003e \u003ch2\u003e2.4 Structure-activity relationship of antiviral activity\u003c/h2\u003e \u003cp\u003eFrom the test data of antiviral activity, it can be seen that substituents had great influence on the biological activity of compounds. According to the anti-TMV activity shown in Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e, the structure-activity relationship (SAR) was analyzed. H, -OCH\u003csub\u003e3\u003c/sub\u003e, -CF\u003csub\u003e3\u003c/sub\u003e and -CH\u003csub\u003e3\u003c/sub\u003e groups at the R position are beneficial to the curative and protective activities of the target compound against TMV. For example, the curative activities of \u003cb\u003eW7\u003c/b\u003e (R\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;5-Br, R\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;H), \u003cb\u003eW16\u003c/b\u003e (R\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;5-OCH\u003csub\u003e3\u003c/sub\u003e, R\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;H), \u003cb\u003eW18\u003c/b\u003e (R\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;5-OCH\u003csub\u003e3\u003c/sub\u003e, R\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;4-CH\u003csub\u003e3\u003c/sub\u003e), \u003cb\u003eW20\u003c/b\u003e (R\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;5-OCH\u003csub\u003e3\u003c/sub\u003e, R\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;3-OCH\u003csub\u003e3\u003c/sub\u003e) were 75.2, 64.5, 68.4 and 75.1%, respectively. The protective activities were 79.9, 66.5, 75.3 and 82.7%, respectively, which were superior to other substituents. It was worth noting that when R\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;5-OCH\u003csub\u003e3\u003c/sub\u003e and R\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;3-OCH\u003csub\u003e3\u003c/sub\u003e, the curative and protective effects are the best. For example, the curative and protective activities are \u003cb\u003eW20\u003c/b\u003e (R\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;5-OCH\u003csub\u003e3\u003c/sub\u003e, R\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;3-OCH\u003csub\u003e3\u003c/sub\u003e)\u0026thinsp;\u0026gt;\u0026thinsp;\u003cb\u003eW7\u003c/b\u003e (R\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;5-Br, R\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;H)\u0026thinsp;\u0026gt;\u0026thinsp;\u003cb\u003eW19\u003c/b\u003e(R\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;5-OCH\u003csub\u003e3\u003c/sub\u003e, R\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;4-Cl-Ph)\u0026thinsp;\u0026gt;\u0026thinsp;\u003cb\u003eW14\u003c/b\u003e (R\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;5-Cl, R\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;4-Cl-Ph). To sum up, \u003cb\u003eW20\u003c/b\u003e (R\u003csub\u003e1\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;5-OCH\u003csub\u003e3\u003c/sub\u003e, R\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;3-OCH\u003csub\u003e3\u003c/sub\u003e) had obvious inhibitory effect on TMV. It was speculated that when R\u003csub\u003e1\u003c/sub\u003e and R\u003csub\u003e2\u003c/sub\u003e are electron donor groups, the curative and protective activities of the target compound on TMV can be enhanced. On the contrary, when there was an electron-withdrawing group, its antiviral activity decreases, which can provide an idea of structure-activity relationship.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec7\" class=\"Section2\"\u003e \u003ch2\u003e2.5 Binding ability of \u003cb\u003eW18\u003c/b\u003e, \u003cb\u003eW20\u003c/b\u003e and NNM to TMV-CP\u003c/h2\u003e \u003cp\u003eThe inhibitory effects of \u003cb\u003eW18\u003c/b\u003e, \u003cb\u003eW20\u003c/b\u003e and NNM on TMV-CP were studied by microscale thermophoresis (MST) [\u003cspan citationid=\"CR38\" class=\"CitationRef\"\u003e38\u003c/span\u003e, \u003cspan citationid=\"CR39\" class=\"CitationRef\"\u003e39\u003c/span\u003e], and the results were shown in Table\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e and Fig.\u0026nbsp;\u003cspan refid=\"Fig7\" class=\"InternalRef\"\u003e6\u003c/span\u003e. The dissociation constants K\u003csub\u003ed\u003c/sub\u003e of \u003cb\u003eW18\u003c/b\u003e, \u003cb\u003eW20\u003c/b\u003e and NNM for TMV-CP are 0.38099\u0026thinsp;\u0026plusmn;\u0026thinsp;0.13752 \u003cem\u003e\u0026micro;\u003c/em\u003emol/L, 0.00519\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00259 \u003cem\u003e\u0026micro;\u003c/em\u003emol/L and 1.65320\u0026thinsp;\u0026plusmn;\u0026thinsp;0.42835 \u003cem\u003e\u0026micro;\u003c/em\u003emol/L, respectively. Therefore, the affinity of \u003cb\u003eW20\u003c/b\u003e for TMV-CP was better than that of \u003cb\u003eW18\u003c/b\u003e, and far exceeds that of NNM. The results show that \u003cb\u003eW20\u003c/b\u003e\u0026thinsp;\u0026gt;\u0026thinsp;\u003cb\u003eW18\u003c/b\u003e\u0026thinsp;\u0026gt;\u0026thinsp;NNM, which was consistent with the preliminary screening results.\u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab3\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 3\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eThe dissociation constant of \u003cb\u003eW18\u003c/b\u003e, \u003cb\u003eW20\u003c/b\u003e and ningnanmycin with TMV-CP\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"2\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\"\u0026plusmn;\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eCompounds\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eKd (\u003cem\u003e\u0026micro;\u003c/em\u003eM)\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW18\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c2\"\u003e \u003cp\u003e0.38099\u0026thinsp;\u0026plusmn;\u0026thinsp;0.13752\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eW20\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c2\"\u003e \u003cp\u003e0.00519\u0026thinsp;\u0026plusmn;\u0026thinsp;0.00259\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eningnanmycin\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\"\u0026plusmn;\" colname=\"c2\"\u003e \u003cp\u003e1. 65320\u0026thinsp;\u0026plusmn;\u0026thinsp;0.42835\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003ctfoot\u003e \u003ctr\u003e\u003ctd colspan=\"2\"\u003e\u003csup\u003ea\u003c/sup\u003eThe commercial antiviral agents ningnanmycin.\u003c/td\u003e\u003c/tr\u003e \u003c/tfoot\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eTable\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e\u003c/p\u003e \u003cp\u003eFigure\u0026nbsp;\u003cspan refid=\"Fig7\" class=\"InternalRef\"\u003e6\u003c/span\u003e.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec8\" class=\"Section2\"\u003e \u003ch2\u003e2.6 Molecular docking of \u003cb\u003eW20\u003c/b\u003e and NNM with TMV‑CP\u003c/h2\u003e \u003cp\u003eIn order to identify TMV-CP recognition sites in \u003cb\u003eW20\u003c/b\u003e and NNM (protein database (PDB) code: 1EI7) [\u003cspan citationid=\"CR35\" class=\"CitationRef\"\u003e35\u003c/span\u003e, \u003cspan citationid=\"CR40\" class=\"CitationRef\"\u003e40\u003c/span\u003e, \u003cspan citationid=\"CR41\" class=\"CitationRef\"\u003e41\u003c/span\u003e], the results of molecular docking are shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig8\" class=\"InternalRef\"\u003e7\u003c/span\u003e. \u003cb\u003eW20\u003c/b\u003e and NNM are bound to TMV-CP in the same active pocket. Among them, \u003cb\u003eW20\u003c/b\u003e has a strong interaction with surrounding residues SER138 (2.83\u0026Aring;), TYR139 (4.67 and 5.20 \u0026Aring;), VAL260 (3.84 and 5.28 \u0026Aring;), GLN257 (0.99 \u0026Aring;), SER255 (2.53 \u0026Aring;), LYS268 (2.46 and 2.67\u0026Aring;), LYS253 (4.09 \u0026Aring;), ASP219 (2.74 \u0026Aring;), GLU222 (2.35\u0026Aring;), GLU131 (2.76 \u0026Aring;), VAL75 (4.56 \u0026Aring;), ARG134 (5.21 \u0026Aring;), ASP266 (4.90 \u0026Aring;) and GLY135 (4.97 \u0026Aring;) in TMV-CP active pocket through conventional hydrogen bond, carbon hydrogen bond, pi-anion and hydrophobic interaction, in which residue LYS268 (2.46 \u0026Aring;), ASP219 (2.74 \u0026Aring;), SER138 (2.83\u0026Aring;), GLU222 (2.35\u0026Aring;) and GLU131 (2.76 \u0026Aring;) and \u003cb\u003eW20\u003c/b\u003e form four strong hydrogen bonds respectively. For commercial NNM, in the active pocket of TMV-CP, it interacts with the surrounding residue GLY135 (2.70 \u0026Aring;), SER138 (2.76, 2.53 and 2.59\u0026Aring;), GLY137 (2.45 \u0026Aring;), SER255 (3.00 \u0026Aring;), ARG134 (1.79 and 2.96 \u0026Aring;), LYS253 (5.16 \u0026Aring;), GLU131 (3.64\u0026Aring;) and PRO254 (1.97 \u0026Aring;) through hydrogen bonding with residue SER138 (2.76, 2.53 and 2.59\u0026Aring;), GLY137 (2.45 \u0026Aring;) and ARG134 (1.79 and 2.96 \u0026Aring;), pi-alkyl and pi-anion. Through the analysis of the above results, the length of the conventional hydrogen bond formed by \u003cb\u003eW20\u003c/b\u003e and TMV-CP was close to that of NNM, but the number of amino acid residues of \u003cb\u003eW20\u003c/b\u003e and TMV-CP was more than that of NNM, which makes the antiviral activity of \u003cb\u003eW20\u003c/b\u003e and TMV-CP better than that of NNM through various modes of action such as carbon hydrogen bond, van der waals, pi-cation, pi-sulfur, pi-pi stacked, alkyl, pi-alkyl and hydrophobic interaction.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eFigure\u0026nbsp;\u003cspan refid=\"Fig8\" class=\"InternalRef\"\u003e7\u003c/span\u003e\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec9\" class=\"Section2\"\u003e \u003ch2\u003e2.7 Analysis characteristics of virus malondialdehyde (MDA) content of \u003cb\u003eW20\u003c/b\u003e\u003c/h2\u003e \u003cp\u003eMalondialdehyde (MDA) content reflects the degree of membrane lipid peroxidation caused by tobacco infestation [\u003cspan citationid=\"CR42\" class=\"CitationRef\"\u003e42\u003c/span\u003e, \u003cspan citationid=\"CR43\" class=\"CitationRef\"\u003e43\u003c/span\u003e]. Changes in MDA content in each test group at days 1, 3, 5 and 7 after inoculation are shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig11\" class=\"InternalRef\"\u003e8\u003c/span\u003e. After inoculation with TMV, the MDA content in tobacco treated with \u003cb\u003eW20\u003c/b\u003e gradually decreased from from the 1\u0026ndash;5 d, reached the lowest value at the 5 d, and began to increase from the 5 to 7 d. Especially on the 5 d, the MDA content of \u003cb\u003eW20\u0026thinsp;+\u0026thinsp;TMV\u003c/b\u003e group was about 50% lower than that of \u003cb\u003eCK\u0026thinsp;+\u0026thinsp;TMV\u003c/b\u003e group. In addition, the MDA content in the \u003cb\u003eW20\u003c/b\u003e group was also lower than that in the \u003cb\u003eCK\u003c/b\u003e group within 1\u0026ndash;7 d. Therefore, \u003cb\u003eW20\u003c/b\u003e can reduce the content of MDA in tobacco plants, effectively prevent TMV infection and reinfection, and improve tobacco disease resistance.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eFigure\u0026nbsp;\u003cspan refid=\"Fig11\" class=\"InternalRef\"\u003e8\u003c/span\u003e.\u003c/p\u003e \u003c/div\u003e"},{"header":"3 Conclusion","content":"\u003cp\u003eTo sum up, a series of indole derivatives containing quinoline were synthesized based on the principle of active splicing, and their biological activities were tested. The results of antiviral test show that most compounds had obvious therapeutic, protective and inactivation effects on TMV. The results show that the EC\u003csub\u003e50\u003c/sub\u003e value of \u003cb\u003eW7\u003c/b\u003e, \u003cb\u003eW18\u003c/b\u003e, \u003cb\u003eW20\u003c/b\u003e and \u003cb\u003eW21\u003c/b\u003e were \u003cb\u003e86.6\u003c/b\u003e, \u003cb\u003e137.3\u003c/b\u003e, \u003cb\u003e84.4\u003c/b\u003e and \u003cb\u003e168.4\u003c/b\u003e \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL, respectively, in terms of curative activity, which were superior to the control agent NNM (205.1 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL). The EC\u003csub\u003e50\u003c/sub\u003e value of \u003cb\u003eW7\u003c/b\u003e, \u003cb\u003eW8\u003c/b\u003e, \u003cb\u003eW16\u003c/b\u003e, \u003cb\u003eW17\u003c/b\u003e, \u003cb\u003eW18\u003c/b\u003e, \u003cb\u003eW20\u003c/b\u003e and \u003cb\u003eW21\u003c/b\u003e were 76.8, 119.9, 162.7, 101.4, 96.3, 65.7 and 119.6 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL, respectively, in terms of protective activity, which were better than NNM (162.0 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL). The results of MST showed that the K\u003csub\u003ed\u003c/sub\u003e value of \u003cb\u003eW20\u003c/b\u003e combined with TMV-CP was 0.00519 \u003cem\u003e\u0026micro;\u003c/em\u003emol/L, which was better than that of control drug NNM (1.65320 mol/L). The molecular docking study was consistent with the experimental results. Moreover, \u003cb\u003eW20\u003c/b\u003e can reduce the malondialdehyde content of tobacco plants, effectively prevent TMV infection and reinfection, and improve tobacco disease resistance. Therefore, we can further develop indole derivatives containing quinoline as potential drugs, and also provide new ideas and certain theoretical basis for the creation of green pesticides.\u003c/p\u003e"},{"header":"4 Materials and methods","content":"\u003cdiv id=\"Sec12\" class=\"Section2\"\u003e \u003ch2\u003e4.1 Instruments and chemicals\u003c/h2\u003e \u003cp\u003eThe melting point of the compound was determined by the X-4B (Shanghai Instrument, Electrophysical and Optical Instrument Co., Ltd., China) microscopic digital melting point tester. \u003csup\u003e1\u003c/sup\u003eH, \u003csup\u003e13\u003c/sup\u003eC and \u003csup\u003e19\u003c/sup\u003eF NMR spectra were obtained by JEOL-ECX500 (Japanese electronics co., LTD, Japan) and ASCEND400 (Bruker, Germany), and high-resolution mass spectrometry was obtained by Thermo Scientic Q Exactive (Thermo Fisher Scientific, USA) high-resolution mass spectrometer. The N-5000 UV spectrophotometer (Shanghai Yoke Instrument Co., Ltd., China) was used to detect malondialdehyde (MDA) content. the data of the crystal were collected by an X-ray diffractometer (Bruker, Germany). All reagents and solvents were commercially purchased and were analytically pure, with no purification required and ready for use. Thin layer chromatography (TLC) analysis was performed using a WFH-203B (Shanghai Jinko Industry Co., Ltd., China) ultraviolet analyzer.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec13\" class=\"Section2\"\u003e \u003ch2\u003e4.2 General synthetic procedure for key intermediates \u003cb\u003e1\u0026ndash;4\u003c/b\u003e\u003c/h2\u003e \u003cdiv id=\"Sec14\" class=\"Section3\"\u003e \u003ch2\u003e4.2.1 Synthesis of intermediate \u003cb\u003e1\u003c/b\u003e\u003c/h2\u003e \u003cp\u003e1-(2-aminophenyl)ethan-1-one (7.40 mmol) and 30 mL of dichloromethane were added to a round-bottomed flask, and substituted benzoyl chloride (8.88 mmol) was slowly added under magnetic stirring. At the end of the reaction 90 mL of water was added and extracted with dichloromethane in three fractions, after collecting the organic phase and removing the solvent under vacuum. Then recrystallized in (\u003cem\u003eV\u003c/em\u003e (petroleum ether): \u003cem\u003eV\u003c/em\u003e (ethyl acetate)\u0026thinsp;=\u0026thinsp;4:1) mixed solvent to obtain white needle-like crystals of intermediate \u003cb\u003e1.\u003c/b\u003e\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec15\" class=\"Section3\"\u003e \u003ch2\u003e4.2.2 Synthesis of intermediate \u003cb\u003e2\u003c/b\u003e\u003c/h2\u003e \u003cp\u003eIntermediate \u003cb\u003e1\u003c/b\u003e (3.95 mmol) and 1,4-dioxane (30 mL) were placed in a three-necked flask and stirred at reflux for 2 h at 110\u0026deg;C with the addition of NaOH (11.84 mmol). After completion of the reaction, the solvent was removed under vacuum and the reaction mixture was added to about 200 mL of H\u003csub\u003e2\u003c/sub\u003eO, 10% aqueous HCl was added into the above mixture until pH 6\u0026ndash;7, filtered by pumping, and then the residue was washed with H\u003csub\u003e2\u003c/sub\u003eO and a mixture of dichloromethane and ethyl acetate (\u003cem\u003eV\u003c/em\u003e: \u003cem\u003eV\u003c/em\u003e\u0026thinsp;=\u0026thinsp;1:1) to give Intermediate \u003cb\u003e2\u003c/b\u003e.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec16\" class=\"Section3\"\u003e \u003ch2\u003e4.2.3 Synthesis of intermediate \u003cb\u003e3\u003c/b\u003e\u003c/h2\u003e \u003cp\u003eIntermediate \u003cb\u003e2\u003c/b\u003e (4.25 mmol) and anhydrous pyridine (30 mL) were placed in a three-necked flask, diphosphorus pentasulfide (8.50 mmol) was slowly added to the mixture and the reaction system was refluxed at 110\u0026deg;C for about 5 h. After completion of the reaction, the reaction mixture was added to about 200 mL of H\u003csub\u003e2\u003c/sub\u003eO and stirred for a few minutes, the mixture was filtered and the solid product obtained was dried at 40\u0026deg;C for 6 h. The crude product was completely dissolved in 200 mL of 10% sodium hydroxide solution, and glacial acetic acid was added to the above mixture until the pH 6\u0026ndash;7. After filtration, the residue was washed with H\u003csub\u003e2\u003c/sub\u003eO and petroleum ether to give intermediate \u003cb\u003e3\u003c/b\u003e [\u003cspan citationid=\"CR44\" class=\"CitationRef\"\u003e44\u003c/span\u003e, \u003cspan citationid=\"CR45\" class=\"CitationRef\"\u003e45\u003c/span\u003e].\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec17\" class=\"Section3\"\u003e \u003ch2\u003e4.2.4 Synthesis of intermediate \u003cb\u003e4\u003c/b\u003e\u003c/h2\u003e \u003cp\u003eA round-bottomed flask containing of substituted indole (1.53 mmol) and 15 mL DMF was filled with the mixture. Stirring continuously, NaH (4.59 mmol) was gradually added, and after 20 min of stirring, epibromohydrin (4.59 mmol) was added. The mixture was then heated to 45\u0026deg;C and refluxed for a duration of 12 h. Following heating, the reactant was mixed with 90 milliliters of distilled water and extracted three times using ethyl acetate. To produce oily compound intermediate \u003cb\u003e4\u003c/b\u003e, gather the lower liquid, wash it three times with saturated brine, and then dry, filter, and spin-dry it [\u003cspan citationid=\"CR46\" class=\"CitationRef\"\u003e46\u003c/span\u003e].\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec18\" class=\"Section3\"\u003e \u003ch2\u003e4.2.5 Synthesis of target compounds \u003cb\u003eW1-W21\u003c/b\u003e\u003c/h2\u003e \u003cp\u003eK\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e (13.86 mmol) and 20 mL of DMF were added to a round-bottom flask along with Intermediate \u003cb\u003e4\u003c/b\u003e (4.62 mmol). Intermediate \u003cb\u003e3\u003c/b\u003e (5.08 mmol) was added to the reaction mixture after 0.5 h. TLC was used to track the reaction's course for around 10 h at 77\u0026deg;C. TLC was used to carry out the reaction. The reaction was heated, then combined with 90 mL of distilled water and extracted with ethyl acetate. The lower liquid phase was recovered, dried, filtered, and the ethyl acetate solvent was removed after three washes with saturated brine. The resultant product was purified further by column chromatography using a volumetric ratio of petroleum ether to ethyl acetate (15:1) as eluent to obtain \u003cb\u003eW1-W21\u003c/b\u003e ranging from 29\u0026ndash;77%.\u003c/p\u003e \u003cp\u003e1-((2-(2-chlorophenyl)quinolin-4-yl)thio)-3-(1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)propan-2-ol \u003cb\u003e(W1)\u003c/b\u003e. White solid; yield: 42%; m.p. 154.4-155.1 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.17 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.0 Hz, 1H, Ph-H), 8.04 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.2 Hz, 1H, Ph-H), 7.87\u0026ndash;7.77 (m, 1H, Ph-H), 7.73\u0026ndash;7.63 (m, 1H, Ph-H), 7.69\u0026ndash;7.60 (m, 2H, Ph-H), 7.57 (s, 1H, Ph-H), 7.57\u0026ndash;7.47 (m, 3H, Ph-H), 7.47 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.2 Hz, 1H, Indol-2-H), 7.35 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Ph-H), 7.08\u0026ndash;6.98 (m, 1H, Ph-H), 6.97 (t, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.0 Hz, 1H, Ph-H), 6.37 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-3-H), 5.68 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.6 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.44 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.24 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.20\u0026ndash;4.12 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.36 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.21 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 156.18 (s), 146.83 (s), 146.67 (s), 139.32 (s), 136.14 (s), 131.74 (s), 131.59 (s), 130.52 (s), 130.39 (s), 129.98 (s), 129.58 (s), 128.16 (s), 127.48 (s), 127.14 (s), 124.78 (s), 123.25 (s), 121.01 (s), 120.47 (s), 119.03 (s), 117.26 (s), 110.05 (s), 100.66 (s), 68.23 (s), 51.01 (s), 35.38 (s); ESI-HRMS calcd for C\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eClN\u003csub\u003e2\u003c/sub\u003eOS [M་H]\u003csup\u003e་\u003c/sup\u003e445.11386, found 445.11359.\u003c/p\u003e \u003cp\u003e1-((2-(4-chlorophenyl)quinolin-4-yl)thio)-3-(1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)propan-2-ol (\u003cb\u003eW2\u003c/b\u003e). White solid; yield: 37%; m.p. 147.5-180.3 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.27\u0026ndash;8.22 (m, 2H, Ph-H), 8.14 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.0 Hz, 1H, Ph-H), 8.05 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.2 Hz, 1H, Ph-H), 7.84 (s, 1H, Ph-H), 7.82\u0026ndash;7.78 (m, 1H, Ph-H), 7.66\u0026ndash;7.60 (m, 3H, Ph-H), 7.55\u0026ndash;7.48 (m, 2H, Ph-H), 7.40 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-2-H), 7.05\u0026ndash;6.96 (m, 2H, Ph-H), 6.44 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-3-H), 5.72 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.6 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.49 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.27 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.19\u0026ndash;4.13 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.53 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.34 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 154.07 (s), 148.12 (s), 146.78 (s), 137.44 (s), 136.12 (s), 134.74 (s), 130.52 (s), 130.01 (s), 129.73 (s), 129.23 (s), 128.91 (s), 128.22 (s), 126.83 (s), 125.07 (s), 123.27 (s), 120.99 (s), 120.53 (s), 119.05 (s), 113.42 (s), 110.02 (s), 100.68 (s), 68.36 (s), 51.19 (s), 35.46 (s); ESI-HRMS calcd for C\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eClN\u003csub\u003e2\u003c/sub\u003eOS [M་H]\u003csup\u003e་\u003c/sup\u003e445.11359, found 445.11359.\u003c/p\u003e \u003cp\u003e1-((2-(2-fluorophenyl)quinolin-4-yl)thio)-3-(1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)propan-2-ol (\u003cb\u003eW3\u003c/b\u003e). White solid; yield: 65%; m.p. 160.1-160.5 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.16 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.3 Hz, 1H, Ph-H), 8.06 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.2 Hz, 1H, Ph-H), 7.97\u0026ndash;7.92 (m, 1H, Ph-H), 7.82 (t, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.2 Hz, 1H, Ph-H), 7.70\u0026ndash;7.65 (m, 2H, Ph-H), 7.61\u0026ndash;7.55 (m, 1H, Ph-H), 7.50 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 2H, Ph-H), 7.44\u0026ndash;7.38 (m, 2H, Ph-H), 7.36 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.2 Hz, 1H, Indol-2-H), 7.04 (t, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 6.98 (t, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.4 Hz, 1H, Ph-H), 6.40 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-3-H), 5.69 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.7 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.46 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.25 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.20\u0026ndash;4.13 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.44 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.23 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 161.51 (s), 159.53 (s), 153.22 (s), 147.71 (s), 147.29 (s), 136.56 (s), 131.92 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.8 Hz), 130.87 (s), 130.43 (s), 130.01 (s), 128.58 (s), 127.99 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;12.5 Hz), 127.49 (s), 125.34 (d, \u003csup\u003e4\u003c/sup\u003e\u003cem\u003eJ\u003c/em\u003e\u003csub\u003eC\u0026minus;F\u003c/sub\u003e = 3.8 Hz), 125.25 (s), 123.65 (s), 121.42 (s), 120.87 (s), 119.44 (s), 117.30 (d, \u003csup\u003e3\u003c/sup\u003e\u003cem\u003eJ\u003c/em\u003e\u003csub\u003eC\u0026minus;F\u003c/sub\u003e = 6.3 Hz), 116.98 (s), 116.80 (s), 110.44 (s), 101.08 (s), 68.62 (s), 51.49 (s), 35.90 (s); \u003csup\u003e19\u003c/sup\u003eF NMR (470 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e -116.46; ESI-HRMS calcd for C\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eFN\u003csub\u003e2\u003c/sub\u003eOS [M་H]\u003csup\u003e་\u003c/sup\u003e429.14313, found 429.14314.\u003c/p\u003e \u003cp\u003e1-(1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-(m-tolyl)quinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW4\u003c/b\u003e). White solid; yield: 54%; m.p. 119.0-119.2 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.14 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10 Hz, 1H, Ph-H), 8.09 (s, 1H, Ph-H), 8.06 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.1 Hz, 1H, Ph-H), 7.98 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.2 Hz, 1H, Ph-H), 7.86 (s, 1H, Ph-H), 7.81\u0026ndash;7.77 (m, 1H, Ph-H), 7.64\u0026ndash;7.60 (m, 1H, Ph-H), 7.55\u0026ndash;7.50 (m, 2H, Ph-H), 7.46 (t, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.7 Hz, 1H, Ph-H), 7.40 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Ph-H), 7.34 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.4 Hz, 1H, Indol-2-H), 7.04\u0026ndash;6.95 (m, 2H, Ph-H), 6.43 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-3-H), 5.73 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.7 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.51 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.27 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.21\u0026ndash;4.14 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.53 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.34 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 2.46 (s, 3H,-Ph-CH\u003csub\u003e3\u003c/sub\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 155.52 (s), 147.66 (s), 146.91 (s), 138.69 (s), 138.09 (s), 136.13 (s), 130.47 (s), 130.35 (s), 129.99 (s), 129.72 (s), 128.81 (s), 128.21 (s), 127.99 (s), 126.57 (s), 125.04 (s), 124.73 (s), 123.26 (s), 120.99 (s), 120.51 (s), 119.05 (s), 113.79 (s), 110.01 (s), 100.65 (s), 68.38 (s), 51.18 (s), 35.49 (s), 21.34 (s); ESI-HRMS calcd for C\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eOS [M་H]\u003csup\u003e་\u003c/sup\u003e425.16818, found 425.16821.\u003c/p\u003e \u003cp\u003e1-(1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-(p-tolyl)quinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW5\u003c/b\u003e). White solid; yield: 29%; m.p. 158.0-158.3 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.13 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.2 Hz, 3H, Ph-H), 8.04 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.9 Hz, 1H, Ph-H), 7.82 (s, 1H, Ph-H), 7.80\u0026ndash;7.76 (m, 1H, Ph-H), 7.62\u0026ndash;7.58 (m, 1H, Ph-H), 7.54 (t, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.4 Hz, 2H, Ph-H), 7.40 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-2-H), 7.38 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.0 Hz, 2H, Ph-H), 7.06\u0026ndash;6.98 (m, 2H, Ph-H), 6.44 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-3-H), 5.73 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.7 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.50 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.28 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.21\u0026ndash;4.14 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.51 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.33 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 2.41 (s, 3H,-Ph-CH\u003csub\u003e3\u003c/sub\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 155.27 (s), 147.60 (s), 146.91 (s), 139.51 (s), 136.14 (s), 135.87 (s), 130.32 (s), 129.92 (s), 129.73 (s), 129.51 (s), 128.22 (s), 127.38 (s), 126.42 (s), 124.95 (s), 123.23 (s), 121.03 (s), 120.53 (s), 119.06 (s), 113.38 (s), 110.04 (s), 100.68 (s), 68.39 (s), 51.21 (s), 35.48 (s), 21.08 (s); ESI-HRMS calcd for C\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eOS [M་H]\u003csup\u003e་\u003c/sup\u003e425.16821, found 425.16821.\u003c/p\u003e \u003cp\u003e1-(1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-(3-methoxyphenyl)quinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW6\u003c/b\u003e). White solid; yield: 58%; m.p. 117.3-118.1 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.14 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10 Hz, 1H, Ph-H), 8.06 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.3 Hz, 1H, Ph-H), 7.87 (s, 1H, Ph-H), 7.84\u0026ndash;7.82 (m, 1H, Ph-H), 7.82\u0026ndash;7.75 (m, 1H, Ph-H), 7.65\u0026ndash;7.60 (m, 1H, Ph-H), 7.55\u0026ndash;7.47 (m, 1H, Ph-H), 7.55\u0026ndash;7.47 (m, 3H, Ph-H), 7.40 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-2-H), 7.13\u0026ndash;7.09 (m, 1H, Ph-H), 7.05\u0026ndash;6.96 (m, 2H, Ph-H), 6.43 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.5 Hz, 1H, Indol-3-H), 5.72 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.7 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.50 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.27 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.21\u0026ndash;4.13 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.88 (s, 3H, Ph-OCH\u003csub\u003e3\u003c/sub\u003e), 3.54 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.35 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 159.82 (s), 155.19 (s), 147.77 (s), 146.81 (s), 140.22 (s), 136.13 (s), 130.39 (s), 130.06 (s), 130.01 (s), 129.72 (s), 128.21 (s), 126.67 (s), 125.12 (s), 123.26 (s), 121.01 (s), 120.51 (s), 119.89 (s), 119.05 (s), 115.29 (s), 113.89 (s), 112.95 (s), 110.03 (s), 100.66 (s), 68.41 (s), 55.38 (s), 51.21 (s), 35.47 (s); ESI-HRMS calcd for C\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eS [M་H]\u003csup\u003e་\u003c/sup\u003e441.16312, found 441.16313.\u003c/p\u003e \u003cp\u003e1-(5-bromo-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-phenylquinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW7\u003c/b\u003e). White solid; yield: 61%; m.p. 188.8-189.2 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.23\u0026ndash;8.20 (m, 2H, Ph-H), 8.13 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10 Hz, 1H, Ph-H), 8.06 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.9 Hz, 1H, Ph-H), 7.85 (s, 1H, Ph-H), 7.82\u0026ndash;7.78 (m, 1H, Ph-H), 7.73 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.0 Hz, 1H, Ph-H), 7.64\u0026ndash;7.61 (m, 1H, Ph-H), 7.60\u0026ndash;7.57 (m, 2H, Ph-H), 7.56\u0026ndash;7.51 (m, 2H, Ph-H), 7.46 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-2-H), 7.13 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5 Hz, 1H, Ph-H), 6.44 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-3-H), 5.73 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.6 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.50 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.28 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.18\u0026ndash;4.11 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.54 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.32 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 155.38 (s), 147.74 (s), 146.90 (s), 138.70 (s), 134.98 (s), 131.30 (s), 130.40 (s), 130.04 (s), 130.02 (s), 129.82 (s), 128.92 (s), 127.49 (s), 126.63 (s), 125.02 (s), 123.42 (s), 123.24 (s), 122.68 (s), 113.68 (s), 112.20 (s), 111.72 (s), 100.43 (s), 68.37 (s), 51.37 (s), 35.41 (s); ESI-HRMS calcd for C\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eBrN\u003csub\u003e2\u003c/sub\u003eOS [M་H]\u003csup\u003e་\u003c/sup\u003e489.06311, found 489.06307.\u003c/p\u003e \u003cp\u003e1-(5-bromo-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-(2-chlorophenyl)quinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW8\u003c/b\u003e). White solid; yield: 75%; m.p. 145.3-145.9 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.16 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.3, 1.3 Hz, 1H, Ph-H), 8.04 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.3 Hz, 1H, Ph-H), 7.84\u0026ndash;7.80 (m, 1H, Ph-H), 7.70\u0026ndash;7.66 (m, 2H, Ph-H), 7.65\u0026ndash;7.62 (m, 2H, Ph-H), 7.56\u0026ndash;7.51 (m, 3H, Ph-H), 7.47 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.7 Hz, 1H, Ph-H), 7.41 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-2-H), 7.14 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10 Hz, 1H, Ph-H), 6.38 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-3-H), 5.68 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.6 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.44 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.24 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.17\u0026ndash;4.10 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.41 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.19 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 156.15 (s), 146.77 (s), 146.66 (s), 139.30 (s), 134.99 (s), 131.74 (s), 131.56 (s), 131.13 (s), 130.52 (s), 130.39 (s), 129.97 (s), 127.48 (s), 127.14 (s), 124.75 (s), 123.43 (s), 123.23 (s), 122.61 (s), 117.24 (s), 112.22 (s), 111.72 (s), 100.43 (s), 68.22 (s), 51.17 (s), 35.30 (s); ESI-HRMS calcd for C\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eBrClN\u003csub\u003e2\u003c/sub\u003eOS [M་H]\u003csup\u003e་\u003c/sup\u003e523.02423, found 523.02410.\u003c/p\u003e \u003cp\u003e1-(5-bromo-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-(4-chlorophenyl)quinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW9\u003c/b\u003e). White solid; yield: 72%; m.p. 162.8-163.3 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.25\u0026ndash;8.21 (m, 2H, Ph-H), 8.13 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.2 Hz, 1H, Ph-H), 8.04 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.3 Hz, 1H, Ph-H), 7.82\u0026ndash;7.78 (m, 2H, Ph-H), 7.72 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.0 Hz, 1H, Ph-H), 7.65\u0026ndash;7.60 (m, 3H, Ph-H), 7.51 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.7 Hz, 1H, Ph-H), 7.46 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-2-H), 7.14 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10 Hz, 1H, Ph-H), 6.44 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-3-H), 5.73 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.6 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.48 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.28 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.18\u0026ndash;4.11 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.52 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.33 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 154.08 (s), 148.07 (s), 146.78 (s), 137.45 (s), 134.98 (s), 134.75 (s), 131.27 (s), 130.51 (s), 130.04 (s), 130.00 (s), 129.20 (s), 128.91 (s), 126.82 (s), 125.06 (s), 123.44 (s), 123.26 (s), 122.68 (s), 113.47 (s), 112.18 (s), 111.72 (s), 100.46 (s), 68.37 (s), 51.35 (s), 35.42 (s); ESI-HRMS calcd for C\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eBrClN\u003csub\u003e2\u003c/sub\u003eOS [M་H]\u003csup\u003e་\u003c/sup\u003e523.02423, found 523.02410.\u003c/p\u003e \u003cp\u003e1-(5-bromo-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-(p-tolyl)quinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW10\u003c/b\u003e). White solid; yield: 63%; m.p. 166.9-167.5 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.12\u0026ndash;8.09 (m, 3H, Ph-H), 8.03 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.2 Hz, 1H, Ph-H), 7.81\u0026ndash;7.76 (m, 2H, Ph-H), 7.73 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.0 Hz, 1H, Ph-H), 7.62\u0026ndash;7.58 (m, 1H, Ph-H), 7.52 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.7 Hz, 1H, Ph-H), 7.46 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-2-H), 7.38 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.0 Hz, 2H, Ph-H), 7.14 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10 Hz, 1H, Ph-H), 6.44 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-3-H), 5.73 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.5 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.49 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.28 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.18\u0026ndash;4.11 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.52 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.30 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 2.42 (s, 3H,-Ph-CH\u003csub\u003e3\u003c/sub\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 155.28 (s), 147.53 (s), 146.91 (s), 139.48 (s), 135.89 (s), 134.98 (s), 131.28 (s), 130.31 (s), 130.04 (s), 129.91 (s), 129.52 (s), 127.35 (s), 126.41 (s), 124.93 (s), 123.46 (s), 123.22 (s), 122.68 (s), 113.45 (s), 112.19 (s), 111.73 (s), 100.44 (s), 68.34 (s), 51.38 (s), 35.42 (s), 21.07 (s); ESI-HRMS calcd for C\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e23\u003c/sub\u003eBrN\u003csub\u003e2\u003c/sub\u003eOS [M་H]\u003csup\u003e་\u003c/sup\u003e503.07874, found 503.07872.\u003c/p\u003e \u003cp\u003e1-(5-chloro-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-phenylquinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW11\u003c/b\u003e). White solid; yield: 52%; m.p. 156.6-157.1 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.23\u0026ndash;8.20 (m, 2H, Ph-H), 8.13 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 8.06 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.9 Hz, 1H, Ph-H), 7.85 (s, 1H, Ph-H), 7.82\u0026ndash;7.78 (m, 1H, Ph-H), 7.64\u0026ndash;7.61 (m, 1H, Ph-H), 7.61\u0026ndash;7.56 (m, 3H, Ph-H), 7.56\u0026ndash;7.52 (m, 2H, Ph-H), 7.48 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-2-H), 7.03 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 6.44 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.0 Hz, 1H, Indol-3-H), 5.73 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.6 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.50 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.28 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.19\u0026ndash;4.12 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.53 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.37 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 155.38 (s), 147.74 (s), 146.90 (s), 138.70 (s), 134.75 (s), 131.45 (s), 130.38 (s), 130.02 (s), 129.82 (s), 129.32 (s), 128.90 (s), 127.48 (s), 126.62 (s), 125.02 (s), 123.76 (s), 123.24 (s), 120.90 (s), 119.63 (s), 113.67 (s), 111.71 (s), 100.51 (s), 68.39 (s), 51.39 (s), 35.42 (s); ESI-HRMS calcd for C\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eClN\u003csub\u003e2\u003c/sub\u003eOS [M་H]\u003csup\u003e་\u003c/sup\u003e445.11362, found 445.11359.\u003c/p\u003e \u003cp\u003e1-(5-chloro-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-(4-(trifluoromethyl)phenyl)quinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW12\u003c/b\u003e). White solid; yield: 49%; m.p. 126.6-126.8 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.39 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.0 Hz, 2H, Ph-H), 8.17\u0026ndash;8.13 (m, 1H, Ph-H), 8.08 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.0 Hz, 1H, Ph-H), 7.92 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.2 Hz, 2H, Ph-H), 7.86 (s, 1H, Ph-H), 7.85\u0026ndash;7.80 (m, 1H, Ph-H), 7.69\u0026ndash;7.64 (m, 1H, Ph-H), 7.57 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.1 Hz, 1H, Ph-H), 7.55 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.7 Hz, 1H, Ph-H), 7.48 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-2-H), 7.01 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 6.44 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.4 Hz, 1H, Indol-3-H), 5.74 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.5 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.48 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.28 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.19\u0026ndash;4.11 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.55 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.32 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 154.25 (s), 148.80 (s), 147.17 (s), 142.95 (s), 135.15 (s), 131.86 (s), 131.05 (s), 130.57 (s), 129.73 (s), 128.63 (s), 127.58 (s), 126.18 (s), 125.66 (s), 125.3 (dd, \u003csup\u003e3\u003c/sup\u003e\u003cem\u003eJ\u003c/em\u003e\u003csub\u003e\u003cem\u003eC\u0026minus;F\u003c/em\u003e\u003c/sub\u003e = 4.18 Hz), 124.16 (s), 123.69 (s), 121.31 (s), 120.03 (s), 114.26 (s), 112.10 (s), 100.95 (s), 68.75 (s), 51.79 (s), 35.85 (s); \u003csup\u003e19\u003c/sup\u003eF NMR (470 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e -60.93; ESI-HRMS calcd for C\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eClF\u003csub\u003e3\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eOS [M་H]\u003csup\u003e་\u003c/sup\u003e513.10107, found 513.10097.\u003c/p\u003e \u003cp\u003e1-(5-chloro-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-(2,4-dichlorophenyl)quinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW13\u003c/b\u003e). White solid; yield: 80%; m.p. 145.5-145.9 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.15 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.9 Hz, 1H, Ph-H), 8.04 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.2 Hz, 1H, Ph-H), 7.84\u0026ndash;7.80 (m, 2H, Ph-H), 7.72\u0026ndash;7.64 (m, 2H, Ph-H), 7.60 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 7.54 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.1 Hz, 1H, Ph-H), 7.51 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;9.3 Hz, 2H, Ph-H), 7.43 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-2-H), 7.03 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 6.39 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-3-H), 5.69 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.6 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.43 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.25 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.17\u0026ndash;4.09 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.35 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.18 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 155.09 (s), 147.07 (s), 146.62 (s), 138.16 (s), 134.75 (s), 134.31 (s), 132.99 (s), 132.65 (s), 131.29 (s), 130.49 (s), 129.96 (s), 129.43 (s), 129.25 (s), 127.70 (s), 127.29 (s), 124.79 (s), 123.77 (s), 123.23 (s), 120.93 (s), 119.55 (s), 117.00 (s), 111.71 (s), 100.54 (s), 68.21 (s), 51.21 (s), 35.33 (s); ESI-HRMS calcd for C\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e19\u003c/sub\u003eCl\u003csub\u003e3\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eOS [M་H]\u003csup\u003e་\u003c/sup\u003e513.03613, found 513.03564.\u003c/p\u003e \u003cp\u003e1-(5-chloro-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-(4-chlorophenyl)quinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW14\u003c/b\u003e). White solid; yield: 37%; m.p. 155.1-155.4 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.25\u0026ndash;8.21 (m, 2H, Ph-H), 8.13 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 8.04 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.3 Hz, 1H, Ph-H), 7.83\u0026ndash;7.78 (m, 2H, Ph-H), 7.65\u0026ndash;7.61 (m, 3H, Ph-H), 7.58 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.1 Hz, 1H, Ph-H), 7.55 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.8 Hz, 1H, Ph-H), 7.47 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-2-H), 7.03 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 6.44 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-3-H), 5.73 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.6 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.48 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.28 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.17\u0026ndash;4.11 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.52 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.32 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 154.08 (s), 148.08 (s), 146.78 (s), 137.45 (s), 134.75 (s), 131.44 (s), 130.51 (s), 130.01 (s), 129.32 (s), 129.20 (s), 128.91 (s), 126.82 (s), 125.06 (s), 123.76 (s), 123.26 (s), 120.91 (s), 119.63 (s), 113.47 (s), 111.71 (s), 100.54 (s), 68.38 (s), 51.37 (s), 35.43 (s); ESI-HRMS calcd for C\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eCl\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eOS [M་H]\u003csup\u003e་\u003c/sup\u003e479.07489, found 479.07462.\u003c/p\u003e \u003cp\u003e1-(5-chloro-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-(p-tolyl)quinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW15\u003c/b\u003e). White solid; yield: 67%; m.p. 166.7-167.1 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.12\u0026ndash;8.09 (m, 3H, Ph-H), 8.03 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.3 Hz, 1H, Ph-H), 7.80\u0026ndash;7.76 (m, 2H, Ph-H), 7.62\u0026ndash;7.59 (m, 1H, Ph-H), 7.59 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.1 Hz, 1H, Ph-H), 7.56 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.8 Hz, 1H, Ph-H), 7.47 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-2-H), 7.37 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.0 Hz, 2H, Ph-H), 7.03 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 6.44 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-3-H), 5.73 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.6 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.49 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.29 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.19\u0026ndash;4.11 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.51 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.31 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 2.41 (s, 3H,-Ph-CH\u003csub\u003e3\u003c/sub\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 155.30 (s), 147.54 (s), 146.92 (s), 139.49 (s), 135.90 (s), 134.76 (s), 131.43 (s), 130.31 (s), 129.91 (s), 129.51 (s), 129.32 (s), 127.35 (s), 126.41 (s), 124.94 (s), 123.77 (s), 123.22 (s), 120.94 (s), 119.64 (s), 113.47 (s), 111.71 (s), 100.53 (s), 68.38 (s), 51.40 (s), 35.44 (s), 21.06 (s); ESI-HRMS calcd for C\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e23\u003c/sub\u003eClN\u003csub\u003e2\u003c/sub\u003eOS [M་H]\u003csup\u003e་\u003c/sup\u003e459.12927, found 459.12924.\u003c/p\u003e \u003cp\u003e1-(5-methoxy-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-phenylquinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW16\u003c/b\u003e). White solid; yield: 33%; m.p. 166.1-166.5 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.25\u0026ndash;8.16 (m, 2H, Ph-H), 8.13 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.0 Hz, 1H, Ph-H), 8.05 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.3 Hz, 1H, Ph-H), 7.86\u0026ndash;7.74 (m, 2H, Ph-H), 7.67\u0026ndash;7.57 (m, 1H, Ph-H), 7.63\u0026ndash;7.52 (m, 2H, Ph-H),7.58\u0026ndash;7.49 (m, 1H, Ph-H), 7.41 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.9 Hz, 1H, Indol-2-H), 7.35 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.0 Hz, 1H, Ph-H), 7.04 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.5 Hz, 1H, Ph-H), 6.66 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 6.35 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.0 Hz, 1H, Indol-3-H), 5.71 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.6 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.44 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.24 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.18\u0026ndash;4.11 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.72 (s, 3H, Indol-5-OCH\u003csub\u003e3\u003c/sub\u003e), 3.50 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.30 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 155.36 (s), 153.49 (s), 147.79 (s), 146.90 (s), 138.68 (s), 131.41 (s), 130.39 (s), 130.12 (s), 130.02 (s), 129.82 (s), 128.90 (s), 128.60 (s), 127.49 (s), 126.62 (s), 125.02 (s), 123.24 (s), 113.58 (s), 111.12 (s), 110.72 (s), 102.21 (s), 100.37 (s), 68.41 (s), 55.39 (s), 51.37 (s), 35.46 (s); ESI-HRMS calcd for C\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eS [M་H]\u003csup\u003e་\u003c/sup\u003e441.16327, found 441.16313.\u003c/p\u003e \u003cp\u003e1-(5-methoxy-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-(m-tolyl)quinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW17\u003c/b\u003e). White solid; yield: 29%; m.p. 142.8-143.2 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.13 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.4 Hz, 1H, Ph-H), 8.09 (s, 1H, Ph-H), 8.06 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.9 Hz, 1H, Ph-H), 7.97 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.0 Hz, 1H, Ph-H), 7.83(s, 1H, Ph-H), 7.81\u0026ndash;7.77 (m, 1H, Ph-H), 7.64\u0026ndash;7.60 (m, 1H, Ph-H), 7.46 (t, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.6 Hz, 1H, Ph-H), 7.40 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.9 Hz, 1H, Indol-2-H), 7.34 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.2 Hz, 2H, Ph-H), 7.03 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.4 Hz, 1H, Ph-H), 6.64 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 6.34 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.0 Hz, 1H, Indol-3-H), 5.71 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.7 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.45 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.23 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.18\u0026ndash;4.10 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.71 (s, 3H, Indol-5-OCH\u003csub\u003e3\u003c/sub\u003e), 3.50 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.31 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 2.46 (s, 3H,-Ph-CH\u003csub\u003e3\u003c/sub\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 155.51 (s), 153.48 (s), 147.66 (s), 146.91 (s), 138.69 (s), 138.10 (s), 131.41 (s), 130.46 (s), 130.36 (s), 130.11 (s), 129.99 (s), 128.81 (s), 128.60 (s), 128.00 (s), 126.57 (s), 125.04 (s), 124.72 (s), 123.26 (s), 113.79 (s), 111.08 (s), 110.69 (s), 102.20 (s), 100.34 (s), 68.40 (s), 55.37 (s), 51.34 (s), 35.47 (s), 21.33 (s); ESI-HRMS calcd for C\u003csub\u003e28\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eS [M་H]\u003csup\u003e་\u003c/sup\u003e455.17889, found 455.17878.\u003c/p\u003e \u003cp\u003e1-(5-methoxy-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-(p-tolyl)quinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW18\u003c/b\u003e). White solid; yield: 56%; m.p. 143.9-144.3 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.13\u0026ndash;8.09 (m, 3H, Ph-H), 8.03 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.3 Hz, 1H, Ph-H), 7.80\u0026ndash;7.75 (m, 2H, Ph-H), 7.62\u0026ndash;7.58 (m, 1H, Ph-H), 7.41 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.8 Hz, 1H, Indol-2-H), 7.39\u0026ndash;7.33 (m, 3H, Ph-H), 7.04 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.4 Hz, 1H, Ph-H), 6.67 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 6.35 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-3-H), 5.71 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.6 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.44 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.24 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.17\u0026ndash;4.11 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.72 (s, 3H, Indol-5-OCH\u003csub\u003e3\u003c/sub\u003e), 3.47 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.29 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 2.41 (s, 3H, -Ph-CH\u003csub\u003e3\u003c/sub\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 155.26 (s), 153.49 (s), 147.60 (s), 146.91 (s), 139.49 (s), 135.86 (s), 131.43 (s), 130.32 (s), 130.11 (s), 129.92 (s), 129.51 (s), 128.60 (s), 127.36 (s), 126.42 (s), 124.94 (s), 123.22 (s), 113.33 (s), 111.11 (s), 110.73 (s), 102.23 (s), 100.38 (s), 68.40 (s), 55.36 (s), 51.38 (s), 35.47 (s), 21.07 (s); ESI-HRMS calcd for C\u003csub\u003e28\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eS [M་H]\u003csup\u003e་\u003c/sup\u003e455.17883, found 455.17878.\u003c/p\u003e \u003cp\u003e1-((2-(4-chlorophenyl)quinolin-4-yl)thio)-3-(5-methoxy-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)propan-2-ol (\u003cb\u003eW19\u003c/b\u003e). White solid; yield: 77%; m.p. 159.5-159.8 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.20 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.3 Hz, 2H, Ph-H), 8.12 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.4 Hz, 1H, Ph-H), 8.04 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.3 Hz, 1H, Ph-H), 7.85\u0026ndash;7.74 (m, 2H, Ph-H), 7.62 (t, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.4 Hz, 3H, Ph-H), 7.39 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.9 Hz, 1H, Ph-H), 7.34 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.0 Hz, 1H, Indol-2-H), 7.03 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.4 Hz, 1H, Ph-H), 6.65 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 6.35 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.0 Hz, 1H, Indol-3-H), 5.72 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.6 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.42 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.23 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.16\u0026ndash;4.09 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.72 (s, 3H, Indol-5-OCH\u003csub\u003e3\u003c/sub\u003e), 3.51 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.29 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 154.08 (s), 153.50 (s), 148.17 (s), 146.80 (s), 137.45 (s), 134.76 (s), 131.44 (s), 130.57 (s), 130.15 (s), 130.03 (s), 129.22 (s), 128.94 (s), 128.64 (s), 126.87 (s), 125.09 (s), 123.28 (s), 113.35 (s), 111.13 (s), 110.75 (s), 102.26 (s), 100.43 (s), 68.40 (s), 55.39 (s), 51.39 (s), 35.48 (s); ESI-HRMS calcd for C\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e23\u003c/sub\u003eClN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eS [M་H]\u003csup\u003e་\u003c/sup\u003e475.12448, found 475.12415.\u003c/p\u003e \u003cp\u003e1-(5-methoxy-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-(3-methoxyphenyl)quinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW20\u003c/b\u003e). White solid; yield: 63%; m.p. 167.1-167.4 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.13 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.2 Hz, 1H, Ph-H), 8.06 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.8 Hz, 1H, Ph-H), 7.85\u0026ndash;7.82 (m, 2H, Ph-H), 7.81\u0026ndash;7.78 (m, 1H, Ph-H), 7.77\u0026ndash;7.74 (m, 1H, Ph-H), 7.64\u0026ndash;7.60 (m, 1H, Ph-H), 7.49 (t, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.9 Hz, 1H, Ph-H), 7.40 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.9 Hz, 1H, Indol-2-H), 7.34 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Ph-H), 7.12 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 7.03 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.5 Hz, 1H, Ph-H), 6.65 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 6.34 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.1 Hz, 1H, Indol-3-H), 5.70 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.6 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.44 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.23 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.19\u0026ndash;4.10 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.88 (s, 3H, -Ph-OCH\u003csub\u003e3\u003c/sub\u003e), 3.71(s, 3H, Indol-5-OCH\u003csub\u003e3\u003c/sub\u003e), 3.51 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.34\u0026ndash;3.29 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 159.83 (s), 155.18 (s), 153.49 (s), 147.77 (s), 146.82 (s), 140.22 (s), 131.41 (s), 130.39 (s), 130.11 (s), 130.05 (s), 130.00 (s), 128.60 (s), 126.67 (s), 125.12 (s), 123.26 (s), 119.89 (s), 115.28 (s), 113.88 (s), 112.96 (s), 111.08 (s), 110.71 (s), 102.23 (s), 100.34 (s), 68.44 (s), 55.38 (s), 51.37 (s), 35.45 (s); ESI-HRMS calcd for C\u003csub\u003e28\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003eS [M་H]\u003csup\u003e་\u003c/sup\u003e471.17404, found 471.17369.\u003c/p\u003e \u003cp\u003e1-(5-methoxy-1\u003cem\u003eH\u003c/em\u003e-indol-1-yl)-3-((2-(4-(trifluoromethyl)phenyl)quinolin-4-yl)thio)propan-2-ol (\u003cb\u003eW21\u003c/b\u003e). White solid; yield: 69%; m.p. 152.9-153.3 ˚С; \u003csup\u003e1\u003c/sup\u003eH NMR (500 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 8.36 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.0 Hz, 2H, Ph-H), 8.14 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.0 Hz, 1H, Ph-H), 8.07 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.4 Hz, 1H, Ph-H), 7.91 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.2 Hz, 2H, Ph-H), 7.83\u0026ndash;7.79 (m, 2H, Ph-H), 7.67\u0026ndash;7.63 (m, 1H, Ph-H), 7.40 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.9 Hz, 1H, Indol-2-H), 7.35 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.0 Hz, 1H, Ph-H), 7.03 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;2.4 Hz, 1H, Ph-H), 6.65 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H, Ph-H), 6.35 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;3.5 Hz, 1H, Indol-3-H), 5.72 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5.6 Hz, 1H, -CH\u003csub\u003e2\u003c/sub\u003eCH(\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eOH\u003c/span\u003e)CH\u003csub\u003e2\u003c/sub\u003e-), 4.43 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.25 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H, -\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003eCH(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 4.19\u0026ndash;4.11 (m, 1H, -CH\u003csub\u003e2\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e(OH)CH\u003csub\u003e2\u003c/sub\u003e-), 3.71(s, 3H, Indol-5-OCH\u003csub\u003e3\u003c/sub\u003e), 3.49 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;15.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e), 3.30 (dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.0 Hz, 1H,-CH\u003csub\u003e2\u003c/sub\u003eCH(OH)\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eCH\u003c/span\u003e\u003csub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e2\u003c/span\u003e\u003c/sub\u003e\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003e-\u003c/span\u003e); \u003csup\u003e13\u003c/sup\u003eC NMR (125 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) \u003cem\u003eδ\u003c/em\u003e 153.78 (s), 153.49 (s), 148.46 (s), 146.77 (s), 142.49 (s), 131.44 (s), 130.65 (s), 130.14 (s), 129.5 (dd, \u003csup\u003e1\u003c/sup\u003e\u003cem\u003eJ\u003c/em\u003e\u003csub\u003e\u003cem\u003eC\u0026minus;F\u003c/em\u003e\u003c/sub\u003e = 252.0 Hz), 128.63 (s), 128.20 (s), 127.18 (s), 125.7 (dd, \u003csup\u003e3\u003c/sup\u003e\u003cem\u003eJ\u003c/em\u003e\u003csub\u003e\u003cem\u003eC\u0026minus;F\u003c/em\u003e\u003c/sub\u003e = 7.5 Hz), 125.50 (s), 125.26 (s), 123.29 (s), 113.69 (s), 111.10 (s), 110.73 (s), 102.23 (s), 100.43 (s), 68.40 (s), 55.33 (s), 51.38 (s), 35.51 (s); ESI-HRMS calcd for C\u003csub\u003e28\u003c/sub\u003eH\u003csub\u003e23\u003c/sub\u003eF\u003csub\u003e3\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eS [M་H]\u003csup\u003e་\u003c/sup\u003e509.15109, found 509.15051.\u003c/p\u003e \u003c/div\u003e \u003c/div\u003e \u003cdiv id=\"Sec19\" class=\"Section2\"\u003e \u003ch2\u003e4.3 Anti-TMV activity assay\u003c/h2\u003e \u003cdiv id=\"Sec20\" class=\"Section3\"\u003e \u003ch2\u003e4.3.1 Curative activity\u003c/h2\u003e \u003cp\u003eSilicon carbide was evenly applied to both sides of the tobacco leaf, and then TMV (500 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL) was brushed vigorously and evenly onto both sides of the leaf with a brush. After 0.5 h of virus infection, the Silicon carbide was rinsed off, and after the leaves were dried, the tips of the heart-leaf tobacco were turned toward themselves, and the left half of the tobacco was used as a blank control, and 500 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL of the target compounds were brushed evenly onto the right half of the tobacco, and the right half of the tobacco was transferred to an environment at 28\u0026deg;C for 2\u0026ndash;3 d. The number of spots on the left and right sides of tobacco was recorded, and then the inhibition rate was calculated by the formula of inhibition rate.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec21\" class=\"Section3\"\u003e \u003ch2\u003e4.3.2 Protective activity\u003c/h2\u003e \u003cp\u003eThe leaf tips of the heartleaf tobacco were turned toward themselves, and the left half of the tobacco leaf was used as a blank control. A solution of the compound (500 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL) was applied to the right side of the tobacco leaf using a brush. After 20\u0026ndash;24 h, carborundum was evenly applied to both sides of the tobacco leaf, and then TMV (500 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL) was applied to both sides of the tobacco leaf. After 0.5 h of virus infection, the silicon carbide was washed off. After completion, the tobacco leaves were transferred to a temperature of 28\u0026deg;C for 2\u0026ndash;3 d. The number of spots on the left and right sides of the tobacco leaves was recorded and the inhibition rate was calculated using the formula for inhibition rate.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec22\" class=\"Section3\"\u003e \u003ch2\u003e\u003cem\u003e4.3.3 Inactivation activity\u003c/em\u003e\u003c/h2\u003e \u003cp\u003eEqual volumes of 1000 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL of the target compound to be tested and 1000 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL of TMV were mixed homogeneously as passivated 500 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL TMV and left for 0.5 h. The left half of the tobacco leaf was used as a blank control, and the left side of the tobacco leaf was dipped into 500 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL TMV virus with a row pen, and the right side of the tobacco leaf was uniformly brushed with 500 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL of TMV that had been passivated for 0.5 h. The carbons were washed off after infection for 0.5 h. The left half of the tobacco leaf was used as a blank control, and the left half of the tobacco leaf was used as a blank control. At the end, the tobacco was transferred to a temperature of 28\u0026deg;C for 2\u0026ndash;3 d. The number of spots on the left and right sides of the tobacco was recorded and the inhibition rate was calculated using the formula for inhibition rate.\u003c/p\u003e \u003c/div\u003e \u003c/div\u003e \u003cdiv id=\"Sec23\" class=\"Section2\"\u003e \u003ch2\u003e\u003cem\u003e4.4 Inhibition rate\u003c/em\u003e\u003c/h2\u003e \u003cp\u003eNNM was utilized as a drug control, while the left side of the tobacco leaf served as a blank control. After counting the number of spots on the left and right tobacco leaves, the following formula was used to determine the anti-TMV inhibition rate:\u003c/p\u003e \u003cp\u003eInhibition rate = [(L\u0026ndash;R)/L] \u0026times; 100%\u003c/p\u003e \u003cp\u003eL: the number of spots on the left half-leaf;\u003c/p\u003e \u003cp\u003eR: the number of spots on the right half-leaf.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec24\" class=\"Section2\"\u003e \u003ch2\u003e4.5 Microscale thermophoresis analysis\u003c/h2\u003e \u003cp\u003eUsing the formula [m (mg)\u0026thinsp;=\u0026thinsp;M (relative molecular mass) \u0026times; 4/1000], the target chemical was weighed and dissolved in 100 \u003cem\u003e\u0026micro;\u003c/em\u003eL DMSO. To prepare the mother liquor, 10 \u003cem\u003e\u0026micro;\u003c/em\u003eL of DMSO dissolved solution was added to a 200 \u003cem\u003e\u0026micro;\u003c/em\u003eL centrifuge tube, followed by 190 \u003cem\u003e\u0026micro;\u003c/em\u003eL of phosphate buffer saline. The 16 centrifuge tubes were numbered 1\u0026ndash;16. 10 \u003cem\u003e\u0026micro;\u003c/em\u003eL of mother liquor was added to No. 1 and No. 2 tubes, and 10 \u003cem\u003e\u0026micro;\u003c/em\u003eL of PBS to No. 2\u0026ndash;16 tubes. The mother liquor in No. 2 centrifuge tube was mixed with PBS. The mixed drug solution in 10 \u003cem\u003e\u0026micro;\u003c/em\u003eL No. 2 centrifuge tube was transferred to No. 3 centrifuge tube. Mix the solution in No. 3 centrifuge tube, then transfer 10 \u003cem\u003e\u0026micro;\u003c/em\u003eL to No. 4 centrifuge tube. Repeat till No.16 centrifuge tube. Finally, 10 \u003cem\u003e\u0026micro;\u003c/em\u003eL of the combined drug solution was removed from the No. 16 centrifuge tube and discarded. To test MST, 10 \u003cem\u003e\u0026micro;\u003c/em\u003eL of labeled TMV-CP-labeled protein was introduced to the 1\u0026ndash;16 labeled drug combination. The mixture was then filled with a customized capillary. Each capillary was measured sequentially.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec25\" class=\"Section2\"\u003e \u003ch2\u003e4.6 Single‑crystal X‑ray diffraction experiments\u003c/h2\u003e \u003cp\u003eThe single crystal X-ray diffraction experiment is to select the crystal with neat appearance and no impurities from \u003cb\u003eW14\u003c/b\u003e for single crystal diffraction experiment. The crystal was placed on a single crystal X-ray diffractometer, and the diffraction data were measured and collected at 273 K using MoKα. According to the collected data, the molecular structure was further determined by structural analysis. Analysis of crystal structure with Olex-2.0 software. In addition, the crystal structure and crystal stacking diagram were obtained by Mercury software.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec26\" class=\"Section2\"\u003e \u003ch2\u003e4.7 Molecular docking\u003c/h2\u003e \u003cp\u003eThe 2D structures of the target compounds \u003cb\u003eW20\u003c/b\u003e and NNM were first drawn using Chemdraw. Then the 2D structure of \u003cb\u003eW20\u003c/b\u003e was converted to 3D structure using Chemdraw 3D. Next, the 3D structure of TMV-CP was downloaded from the PDB database. In addition, TMV-CP was processed in Discovery Studio software to remove water molecules and small molecule ligand structures. Docking and landscaping were performed in with PyMOL.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec27\" class=\"Section2\"\u003e \u003ch2\u003e4.8 Determination of MDA content\u003c/h2\u003e \u003cp\u003eThe content of malondialdehyde (MDA) in tobacco leaves infected with TMV treated with compound \u003cb\u003eW20\u003c/b\u003e was tested by literature method. First, select 15\u0026ndash;20 leaves with good growth and the same leaf size, prune the old leaves and the small leaves at the top, and leave 4\u0026ndash;6 leaves. Dip the medicinal liquid with the concentration of 500 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL with a brush, and smear it evenly on the selected tobacco leaves. The negative control group (DMSO solution) will do the same operation. After 24 h, the TMV virus will be inoculated, and then the 1, 3, 5 and 7 d will be collected respectively. They were divided into CK, CK\u0026thinsp;+\u0026thinsp;TMV, \u003cb\u003eW20\u003c/b\u003e and \u003cb\u003eW20\u003c/b\u003e\u0026thinsp;+\u0026thinsp;TMV groups, and then the absorbance of each sample at 532 and 600 nm was determined according to the method in the kit instructions. The calculation formula of malondialdehyde content was referred to the kit instructions.\u003c/p\u003e \u003c/div\u003e"},{"header":"Declarations","content":"\u003cp\u003e \u003ch2\u003eSupporting information\u003c/h2\u003e \u003cp\u003eThe supporting information includes NMR and HRMS spectrogram data of the target compound and detailed crystal data of \u003cb\u003eW14\u003c/b\u003e.\u003c/p\u003e \u003c/p\u003e\u003cp\u003e \u003ch2\u003eConflicts of interest\u003c/h2\u003e \u003cp\u003eThe authors declare that there are no competing financial interests.\u003c/p\u003e \u003c/p\u003e\u003ch2\u003eAuthor Contribution\u003c/h2\u003e\u003cp\u003eWei Xue，Zhenchao Wang: conceived and designed the experiments. Provide experiment drawing software and method. Bangcan He: performed the experiments, analyzed the data and writing-original draft preparation. Yuzhi Hu, Yishan Qing: evaluated the Antiviral activity of the target compounds. Yufang Zhang, Xingping Luo: provided the material for evaluating the Antiviral activity. All authors have given approval to the final version of the manuscript.\u003c/p\u003e\u003ch2\u003eAcknowledgement\u003c/h2\u003e \u003cp\u003eThe authors gratefully acknowledge the National Nature Science Foundation of China (22007022), the Science Foundation of Guizhou Province (No. 20192452).\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\u003cli\u003e\u003cspan\u003eWang PY, Zhou L, Zhou J, Wu ZB, Xue W, Song BA, Yang S (2016) Synthesis and antibacterial activity of pyridinium-tailored 2,5-substituted-1,3,4-oxadiazole thioether/sulfoxide/sulfone derivatives. 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J Chem 2020:1\u0026ndash;9. \u003cspan class=\"ExternalRef\"\u003e\u003cspan class=\"RefSource\"\u003ehttps://doi.org/10.1155/2020/4358453\u003c/span\u003e\u003cspan address=\"10.1155/2020/4358453\" targettype=\"DOI\" class=\"RefTarget\"\u003e\u003c/span\u003e\u003c/span\u003e\u003c/span\u003e\u003c/li\u003e\u003c/ol\u003e"},{"header":"Scheme ","content":"\u003cp\u003eScheme 1 is available in the Supplementary Files section.\u003c/p\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"molecular-diversity","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"modi","sideBox":"Learn more about [Molecular Diversity](http://link.springer.com/journal/11030)","snPcode":"11030","submissionUrl":"https://submission.nature.com/new-submission/11030/3","title":"Molecular Diversity","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false},"keywords":"indole, quinoline, tobacco mosaic virus, Antiviral activity","lastPublishedDoi":"10.21203/rs.3.rs-3964276/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-3964276/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eA series of indole derivatives containing quinoline structure were designed and synthesized. The synthesized compounds were characterized by NMR and HRMS. And \u003cb\u003eW14\u003c/b\u003e was performed by single crystal X-ray diffraction experiments. The antiviral activity studies showed that some of the target compounds possessed significant activity against tobacco mosaic virus (TMV). In particular, \u003cb\u003eW20\u003c/b\u003e had significant activity. The results of \u003cem\u003ein vivo\u003c/em\u003e anti-TMV activity assay showed that \u003cb\u003eW20\u003c/b\u003e possessed the best curative and protective activities with EC\u003csub\u003e50\u003c/sub\u003e values of 84.4 and 65.7 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL, which were better than ningnanmycin (NNM) 205.1 and 162.0 \u003cem\u003e\u0026micro;\u003c/em\u003eg/mL, respectively. The results of Microscale thermophoresis (MST) showed that \u003cb\u003eW20\u003c/b\u003e had a strong binding affinity for the tobacco mosaic virus coat protein (TMV-CP) with a dissociation constant (K\u003csub\u003ed\u003c/sub\u003e) of 0.00519 \u003cem\u003e\u0026micro;\u003c/em\u003emol/L, which was superior to that of NNM (1. 65320 \u003cem\u003e\u0026micro;\u003c/em\u003emol/L). The molecular docking studies were accordance with the experimental results. In addition, the determination of malondialdehyde (MDA) content in tobacco leaves showed that \u003cb\u003eW20\u003c/b\u003e improved the disease resistance of tobacco. Overall, this study shows that indole derivatives containing quinoline can be used as new antiviral agents for plant viruses for further research.\u003c/p\u003e","manuscriptTitle":"Design, Synthesis and Antiviral Activity of Indole Derivatives Containing Quinoline Moiety","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2024-02-21 20:16:42","doi":"10.21203/rs.3.rs-3964276/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2024-04-25T10:58:14+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2024-04-25T10:02:09+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"8525e0d5-d945-46a9-9fb4-9d2de2b41b08","date":"2024-04-20T19:32:10+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"0fa2f2d1-3fad-414c-830f-7addce3bc305","date":"2024-03-17T10:16:41+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2024-03-12T07:05:11+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"0e644c35-70c8-48e1-b9eb-290e5a153fb6","date":"2024-03-10T05:22:04+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"998231af-771f-4e4f-a3ac-2ae5cf344186","date":"2024-03-09T09:07:07+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"7cdf3672-bc4f-4be2-93ce-3583afe38c34","date":"2024-02-25T19:52:36+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2024-02-22T12:11:04+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2024-02-19T10:02:03+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2024-02-19T09:53:46+00:00","index":"","fulltext":""},{"type":"submitted","content":"Molecular Diversity","date":"2024-02-17T13:56:05+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"molecular-diversity","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"modi","sideBox":"Learn more about [Molecular Diversity](http://link.springer.com/journal/11030)","snPcode":"11030","submissionUrl":"https://submission.nature.com/new-submission/11030/3","title":"Molecular Diversity","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"8a1f6c14-865a-4826-85bd-4a9928d3abdc","owner":[],"postedDate":"February 21st, 2024","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2024-08-01T17:11:51+00:00","versionOfRecord":{"articleIdentity":"rs-3964276","link":"https://doi.org/10.1007/s11030-024-10894-w","journal":{"identity":"molecular-diversity","isVorOnly":false,"title":"Molecular Diversity"},"publishedOn":"2024-07-24 16:16:32","publishedOnDateReadable":"July 24th, 2024"},"versionCreatedAt":"2024-02-21 20:16:42","video":"","vorDoi":"10.1007/s11030-024-10894-w","vorDoiUrl":"https://doi.org/10.1007/s11030-024-10894-w","workflowStages":[]},"version":"v1","identity":"rs-3964276","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-3964276","identity":"rs-3964276","version":["v1"]},"buildId":"qtupq5eGEP_6zYnWcrvyt","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}