Synthesis of novel 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one as antioxidant agent

Synthesis of novel 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one as antioxidant agent | 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 Synthesis of novel 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one as antioxidant agent Chanda W. Awaghade, Meghasham N. Narule (corresponding Author), and 1 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-5317015/v1 This work is licensed under a CC BY 4.0 License Status: Posted Version 1 posted You are reading this latest preprint version Abstract The current study's objective was to create a novel antibacterial agent. Numerous unique heterocyclic O-(β-D-Glucopyranosyl) derivatives have been developed for investigation based on their pharmacological properties in the search for new medications. Synthesis of 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl] -2-phenyl-1, 3-thiazolidin-4-one, which were produced through additions between various acetophenone and urea in a glycosylation. In comparison to standard drugs Norfloxacine and Griseofulvin, these compounds exhibit antibacterial and antifungal activities against bacterial cultures, including Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Proteus vulgaris, and fungal cultures, include Aspergillus Niger and Candida albicans. IR, 1HNMR, and elemental analysis have all verified the compounds' structures. In order to achieve possible pharmacophoric action, these compounds will therefore undergo additional testing. Heterocyclic O-(β -D-Glucopyranosyl) derivatives Thizole Thaizolidine Biological activities etc Figures Figure 1 Figure 2 Figure 3 Figure 4 1. Introduction Due to their wide range of pharmacological effects, numerous O-(β -D-Glucopyranosyl)-4-Thiazolidinones have attracted more attention in the current year's synthesis. These heterocyclic compounds belong to an important class. This effort aims to explore the chemistry of O-(β-D-Glucopyranosyl)-4-Thiazolidinones by synthesizing significant amounts of the compound in a lab setting using both classical and microwave analysis. Known by many other names, heterocyclic compounds are organic chemical compounds with one or more heteroatoms arranged in a ring-like shape. Heterocyclic can be both cyclic and acyclic 1 – 14 . The general structure of heterocyclic is similar to that of cyclic organic compounds, which have only carbon atom in their structure, but the substitute of one or more carbon atoms by heteroatoms gives heterocyclic physico-chemical properties that are distinct from those of all carbon ring analogs 15 – 17 . Heterocyclic involve a wide range of uses, including agrochemical, medicinal, and veterinary 18 . Such compounds are also used in sanitizers, antioxidants, copolymers, corrosion inhibitors, dyestuff 19 , etc. Heterocyclic are currently employed in the production of a wide range of organic chemical substances 20 . Heterocyclic components are found in a number of substances, the majority of which are found in nature. These include morphine, vinblastine, reserpine, alkaloids, and several antibiotics, including cephalosporin and penicillin. The antibacterial activity of schiff bases makes them significant, and their stability and chelating qualities make them exceptional 21 . It is possible to produce innovative medications using schiff bases. Chemists are interested in Schiff base complexes with metal ions because imines have been used for their antiviral, antituberculosis, antibacterial, antifungal, and antimalarial properties 22 . Schiff bases and their metal complexes contain halogens that display antimicrobial activity 23 .4-thiazolidinones have reported for their antibacterial, antiparkinsonian and anti-convalescent activities 24 – 25 . 4-thiazolidinones find their application as local anesthetics and also as moderate tuberculosis agent. Applications of thiazolidinones, a significant class of heterocyclic chemicals, in medicine have been extensively studied. Numerous biological processes 26 – 47 , including signaling, cell-cell communication, molecular and cellular targeting, and hormone production are among the numerous significant types of substances that glycosides constitute. Other glycoside-containing molecules include sweeteners, alkaloids, flavonoids, vitamins, antibiotics and sweeteners. Scheme 1 outlines the series of reactions that result in the creation of desired heterocyclic compounds. In ethanol, thiourea and 4-hydroxyacetophenone combine to generate 4-(2-amino-1, 3-thiazol-4-yl) as the starting material. To create 4-(2-schiffs base), phenol (1) was produced by stirring it with various aldehydes for six hours.-1, 3-thiazol-4-yl After that, phenol (2) underwent cyclization in the presence of glacial acetic acid, producing 3-[4-thiazole-2-yl, 4-(4-hydroxy phenyl)-1]α-D-2, 3, 4, 6-tetra-O-acetyl Glucopyranosyl bromide and 3-thiazolidin-4-one (3) were dissolved in dioxane at 1000C and maintained at this temperature for 4 hours to yield 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl] and 3-thiazolidin-4-one (3).3-thiazolidin-4-one, 2-phenyl-1 (4).In a 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl] solutionthree-thiazolidin-4-one and two-phenyl-1 (4) Newly made 5% sodium methoxide solution was added to 25 mL of dry methanol, and the mixture was allowed to sit at room temperature for 24 hours to yield 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one (5). 2. Experimental 2.1 Materials and methods Using an open capillary tube, the melting points were ascertained, and the results were unchanged. KBr pellets' infrared spectra were captured with a Perkin-Elmer spectrophotometer model 157. The Bruker-300 Varian MHz FT NMR spectrometer was used to record 1H NMR spectra in either CDCl3 or DMSO. TMS was used as the internal standard. Iodine vapors were used to pinpoint the spots, and thin-layer chromatography (TLC) on silica gel G plates was used to evaluate the chemicals' purity. Information on the compounds' characteristics is provided in Tables 3 and 4 . 2.2 Synthesis starting material 2.2.1 4-(2-amino-1, 3-thiazol-4-yl) Phenol Compound (1) was prepared by gradually adding a cold solution of 4-hydroxyacetophenone (0.01 mol) to a thiourea solution (0.01 mol) in ethanol while stirring the mixture continuously (0.01 mol). The reaction mixtures were stirred for a further four hours. Distillation was used to remove the solvent, and the residue was dried, cleaned with petroleum ether, and crystallized from ethanol. Yield 70%:M.P.213 0 C: IR (KBr):3249 (OH), 3153(NH 2 ), 1595(ArH), (C-S-C), (N = C): 1NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), (1H, s, ArH). 2.2.2 Synthesis of 4-(2-schiffs base-1, 3-thiazol-4-yl) Phenol 4-(2-amino-1, 3-thiazol-4-yl) Phenol (1) (0.01mole) and various aldehydes (0.01mole) in methanol were agitated for 6 hours, and the resulting solid was cleaned with ether, dried, and crystallized from ethanol. The reaction liquid was then poured over crushed ice. Yield 70%:M.P.213 0 C: IR (KBr):3249 (OH), 3153(NH 2 ), 1595(ArH), (C-S-C), (N = C): 1NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), (1H, s, ArH). 2.2.3. 3a: Synthesis of 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one Compound 3 (0.01 Mole) is cyclized in 100% ethanol, and a few drops of glacial acetic acid are also added to the experiment. After being stirred for six to seven hours, the reaction liquid was poured over crushed ice. The resulting solid was then dried, washed with ether, and crystallized from ethanol. Yield 71%:M.P.128 0 C: IR (KBr):3143.8 (OH), 2808.2(N = C), 1596.9(ArH), 1508.2(C-S-C), 1444.6(C-C), 1645.2(C = O), 1232.4(C-N-C), 1278.7(C-S-C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), 7.2–7.1(1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0. 2.2.4. 3b: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3141.2 (OH), 2818.1(N = C), 1592.9(ArH), 1511.2(C-S-C), 1444.6(C-C), 1645.2(C = O), 1232.4(C-N-C), 1278.7(C-S-C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), 7.2–7.1(1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0. 2.2.5. 3c: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3143.5 (OH), 2808.4(N = C), 1596.9(ArH), 1528.2(C-S-C), 1442.6(C-C), 1645.2(C = O), 1232.4(C-N-C), 1278.7(C-S-C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), 7.2–7.1(1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0. 2.2.6. 3d: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3133.8 (OH), 2828.2(N = C), 1596.9(ArH), 1538.2(C-S-C), 1434.6(C-C), 1641.2(C = O), 1232.4(C-N-C), 1278.7(C-S-C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), 7.2–7.1(1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0. 2.2.7. 3e: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3043.8 (OH), 2708.2(N = C), 1593.9(ArH), 1558.2(C-S-C), 1445.6(C-C), 1645.2(C = O), 1232.4(C-N-C), 1278.7(C-S-C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), 7.2–7.1(1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0. 2.2.8. 3f: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3143.2 (OH), 2808.1(N = C), 1596.2(ArH), 1508.1(C-S-C), 1444.1(C-C), 1645.3(C = O), 1232.4(C-N-C), 1278.7(C-S-C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), 7.2–7.1(1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0. 2.2.9. 3g: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3153.8 (OH), 2858.2(N = C), 1595.9(ArH), 1508.5(C-S-C), 1444.5(C-C), 1645.5(C = O), 1232.4(C-N-C), 1278.7(C-S-C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), 7.2–7.1(1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0. 2.2.10. 3h: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3123.8 (OH), 2828.2(N = C), 1526.9(ArH), 1528.2(C-S-C), 1444.6(C-C), 1645.2(C = O), 1232.4(C-N-C), 1278.7(C-S-C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), 7.2–7.1(1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0. 2.2.11. 3i: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3143.8 (OH), 2808.2(N = C), 1526.9(ArH), 1528.2(C-S-C), 1444.6(C-C), 1625.2(C = O), 1222.4(C-N-C), 1278.7(C-S-C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), 7.2–7.1(1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0. 2.2.12. 3j: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3143.8 (OH), 2808.2(N = C), 1596.9(ArH), 1508.2(C-S-C), 1444.6(C-C), 1645.2(C = O), 1232.4(C-N-C), 1278.7(C-S-C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), 7.2–7.1(1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 50.1, 52.2, 54.3. 79.4, 74.4, 114.5, 148.5, 126.5, 147.4, 152.5. 2.2.13. 3k: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3143.8 (OH), 2808.2(N = C), 1596.9(ArH), 1508.2(C-S-C), 1444.6(C-C), 1645.2(C = O), 1232.4(C-N-C), 1278.7(C-S-C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), 7.2–7.1(1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 57.2, 57.1, 55.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0. 2.2.14. 3l: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3143.8 (OH), 2808.2(N = C), 1596.9(ArH), 1508.2(C-S-C), 1444.6(C-C), 1645.2(C = O), 1232.4(C-N-C), 1278.7(C-S-C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), 7.2–7.1(1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 59.2, 58.1, 547.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0. 2.3.1. 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 2.3.2. Brominating reagent A 100 mL conical flask was filled with 30 mL of glacial acetic acid, to which 7 mL of molecular bromine was added gradually while the flask was continuously shaken and cooled. For around fifteen minutes, the resulting mixture was let to stand at room temperature. After that, it passed through the glass wool filter. 2.3.3. 2, 3, 4, 6-Tetra- O -acetyl-a-D-glucopyranosyl bromide The brominating reagent was combined with 21.6 g of finely ground glucose pent acetate. The contents of the flask were allowed to settle at room temperature for two hours following the addition. After adding 30 mL of chloroform to the reaction mixture, it was vigorously agitated for approximately 15 minutes. After then, the mixture was put into ice-cold water. The coating of chloroform was removed. It was cleaned multiple times using aqueous sodium bicarbonate to get rid of extra chloric acid, then again with water and sodium metabisulphite to get rid of extra bromine. After that, the layer of chloroform was dried on top of anhydrous calcium chloride. The solvent was then eliminated using vacuum distillation. After distillation, the thick, oily liquid was repeatedly boiled in petroleum ether to produce tetra-O-acetyl-α-D-glucopyranosyl bromide as a solid. Diethyl ether crystallized into it. Yield 15g, M. P. 88 0 C, [a] 20 D = + 197. 2.3.4. 4a: 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 3-[4-(phenyl-4-hydroxy)3-thiazole-2-yl, -1]Dioxane (40 mL) was used to dissolve − 2-phenyl-1, 3-thiazolidin-4-one (0.02 Mol) and a-D-2, 3, 4, 6-tetra-O-acetyl Glucopyranosyl bromide (0.02 Mole) at 1000C. The mixture was then maintained at this temperature for four hours. TLC keeps track of the reaction's progress. Lower pressure was used to extract the solvent. After being dissolved in MeOH-CHCl3 (1:4), the resultant brown syrup was chromatographed on silica gels with a mesh size of 60–120 and eluted with 10% methanol in chloroform. The brown syrup of 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one was obtained. Yield 80%:M.P.172 0 C: IR (KBr):3249 (OH), 3153(NH 2 ), 1595(ArH), (C-S-C), (C-C), (C = O), (N = C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), (1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 162.0. 2.3.5. 4b: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3249 (OH), 3153(NH 2 ), 1595(ArH), (C-S-C), (C-C), (C = O), (N = C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), (1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 162.0. 2.3.6. 4c: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3249 (OH), 3153(NH 2 ), 1595(ArH), (C-S-C), (C-C), (C = O), (N = C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), (1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 67.3, 48.2, 57.3, 59.8, 50.4, 53.3, 53.6. 73.2, 77.2, 131.4, 120.5, 136.6, 140.4, 163.0. 2.3.7. 4d: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3249 (OH), 3153(NH 2 ), 1595(ArH), (C-S-C), (C-C), (C = O), (N = C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), (1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 131.4, 120.5, 123.6, 130.4, 162.0. 2.3.8. 4e: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3249 (OH), 3153(NH 2 ), 1595(ArH), (C-S-C), (C-C), (C = O), (N = C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), (1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 127.6, 147.4, 167.0. 2.3.9. 4f: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3249 (OH), 3153(NH 2 ), 1595(ArH), (C-S-C), (C-C), (C = O), (N = C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), (1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 47.2, 57.5, 57.8, 57.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 167.0. 2.3.10. 4g: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3249 (OH), 3153(NH 2 ), 1595(ArH), (C-S-C), (C-C), (C = O), (N = C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), (1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 57.8, 50.4, 52.3, 57.6. 77.2, 77.2, 111.4, 127.5, 126.6, 140.4, 162.0. 2.3.11. 4h: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3249 (OH), 3153(NH 2 ), 1595(ArH), (C-S-C), (C-C), (C = O), (N = C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), (1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.8, 140.4, 162.8. 2.3.12. 4i: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3249 (OH), 3153(NH 2 ), 1595(ArH), (C-S-C), (C-C), (C = O), (N = C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), (1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.9, 52.9, 53.9. 77.9, 77.2, 191.4, 120.5, 126.6, 140.4, 162.0. 2.3.13. 4j: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3249 (OH), 3153(NH 2 ), 1595(ArH), (C-S-C), (C-C), (C = O), (N = C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), (1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 73.2, 73.2, 131.4, 120.5, 126.6, 140.4, 162.0. 2.3.14. 4k: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3249 (OH), 3153(NH 2 ), 1595(ArH), (C-S-C), (C-C), (C = O), (N = C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), (1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 162.0. 2.3.15. 4l: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3249 (OH), 3153(NH 2 ), 1595(ArH), (C-S-C), (C-C), (C = O), (N = C): 1 NMR (300 MHz DMSO) d 8.7–8.9(4H, s, ArH), 7.4–7.5(5H, s, ArH), (1H, s, OH). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 54.5, 54.8, 54.4, 54.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.4, 140.4, 162.4. 2.4.1. 5a: 2, 3, 5. 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one To a solution of 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one (0.002 Mole) in 25 mL of dry methanol was added freshly prepared 5% sodium methoxide (1.5 mL) solution and the mixture was kept at room temperature for 24 hour. To produce thick, very hygroscopic dark syrup, the reaction mixture was neutralized using ion-exchange resin (Amberlite IR120, Sdfine H + form), filtered, and concentrated in vacuo. Yield 77%:M.P.197 0 C: IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C = O), 1186.1(N = C): 1 NMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M + ) C 23 H 21 O 7 N 2 S 2 , C 18 H 14 O 2 N 2 S 2 (m/z 354), C 12 H 9 ON 2 S 2 (m/z 261), C 6 H 6 O (m/z 94), C 6 H 6 ON 2 S 2 (m/z 86), C 6 H 6 (m/z 78), C 3 H 3 NS (m/z 85), C 3 H 5 OS (m/z89). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 162.0. 2.4.2. 5b: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C = O), 1186.1(N = C): 1 NMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M + ) C 23 H 21 O 7 N 2 S 2 , C 18 H 14 O 2 N 2 S 2 (m/z 354), C 12 H 9 ON 2 S 2 (m/z 261), C 6 H 6 O (m/z 94), C 6 H 6 ON 2 S 2 (m/z 86), C 6 H 6 (m/z 78), C 3 H 3 NS (m/z 85), C 3 H 5 OS (m/z89). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 162.0. 2.4.3. 5c: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C = O), 1186.1(N = C): 1 NMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M + ) C 23 H 21 O 7 N 2 S 2 , C 18 H 14 O 2 N 2 S 2 (m/z 354), C 12 H 9 ON 2 S 2 (m/z 261), C 6 H 6 O (m/z 94), C 6 H 6 ON 2 S 2 (m/z 86), C 6 H 6 (m/z 78), C 3 H 3 NS (m/z 85), C 3 H 5 OS (m/z89). 13 C NMR (300 MHz, DMSO- d 6 ) 67.3, 48.2, 57.3, 59.8, 50.4, 53.3, 53.6. 73.2, 77.2, 131.4, 120.5, 136.6, 140.4, 163.0. 2.4.4. 5d: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C = O), 1186.1(N = C): 1 NMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M + ) C 23 H 21 O 7 N 2 S 2 , C 18 H 14 O 2 N 2 S 2 (m/z 354), C 12 H 9 ON 2 S 2 (m/z 261), C 6 H 6 O (m/z 94), C 6 H 6 ON 2 S 2 (m/z 86), C 6 H 6 (m/z 78), C 3 H 3 NS (m/z 85), C 3 H 5 OS (m/z89). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 131.4, 120.5, 123.6, 130.4, 162.0. 2.4.5. 5e: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C = O), 1186.1(N = C): 1 NMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M + ) C 23 H 21 O 7 N 2 S 2 , C 18 H 14 O 2 N 2 S 2 (m/z 354), C 12 H 9 ON 2 S 2 (m/z 261), C 6 H 6 O (m/z 94), C 6 H 6 ON 2 S 2 (m/z 86), C 6 H 6 (m/z 78), C 3 H 3 NS (m/z 85), C 3 H 5 OS (m/z89). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 127.6, 147.4, 167.0. 2.4.6. 5f: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C = O), 1186.1(N = C): 1 NMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M + ) C 23 H 21 O 7 N 2 S 2 , C 18 H 14 O 2 N 2 S 2 (m/z 354), C 12 H 9 ON 2 S 2 (m/z 261), C 6 H 6 O (m/z 94), C 6 H 6 ON 2 S 2 (m/z 86), C 6 H 6 (m/z 78), C 3 H 3 NS (m/z 85), C 3 H 5 OS (m/z89). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 47.2, 57.5, 57.8, 57.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 167.0. 2.4.7. 5g: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C = O), 1186.1(N = C): 1 NMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M + ) C 23 H 21 O 7 N 2 S 2 , C 18 H 14 O 2 N 2 S 2 (m/z 354), C 12 H 9 ON 2 S 2 (m/z 261), C 6 H 6 O (m/z 94), C 6 H 6 ON 2 S 2 (m/z 86), C 6 H 6 (m/z 78), C 3 H 3 NS (m/z 85), C 3 H 5 OS (m/z89). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 57.8, 50.4, 52.3, 57.6. 77.2, 77.2, 111.4, 127.5, 126.6, 140.4, 162.0. 2.4.8. 5h: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C = O), 1186.1(N = C): 1 NMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M + ) C 23 H 21 O 7 N 2 S 2 , C 18 H 14 O 2 N 2 S 2 (m/z 354), C 12 H 9 ON 2 S 2 (m/z 261), C 6 H 6 O (m/z 94), C 6 H 6 ON 2 S 2 (m/z 86), C 6 H 6 (m/z 78), C 3 H 3 NS (m/z 85), C 3 H 5 OS (m/z89). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.8, 140.4, 162.8. 2.4.9. 5i: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C = O), 1186.1(N = C): 1 NMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M + ) C 23 H 21 O 7 N 2 S 2 , C 18 H 14 O 2 N 2 S 2 (m/z 354), C 12 H 9 ON 2 S 2 (m/z 261), C 6 H 6 O (m/z 94), C 6 H 6 ON 2 S 2 (m/z 86), C 6 H 6 (m/z 78), C 3 H 3 NS (m/z 85), C 3 H 5 OS (m/z89). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.9, 52.9, 53.9. 77.9, 77.2, 191.4, 120.5, 126.6, 140.4, 162.0. 2.4.10. 5j: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C = O), 1186.1(N = C): 1 NMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M + ) C 23 H 21 O 7 N 2 S 2 , C 18 H 14 O 2 N 2 S 2 (m/z 354), C 12 H 9 ON 2 S 2 (m/z 261), C 6 H 6 O (m/z 94), C 6 H 6 ON 2 S 2 (m/z 86), C 6 H 6 (m/z 78), C 3 H 3 NS (m/z 85), C 3 H 5 OS (m/z89). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 73.2, 73.2, 131.4, 120.5, 126.6, 140.4, 162.0. 2.4.11. 5k: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C = O), 1186.1(N = C): 1 NMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M + ) C 23 H 21 O 7 N 2 S 2 , C 18 H 14 O 2 N 2 S 2 (m/z 354), C 12 H 9 ON 2 S 2 (m/z 261), C 6 H 6 O (m/z 94), C 6 H 6 ON 2 S 2 (m/z 86), C 6 H 6 (m/z 78), C 3 H 3 NS (m/z 85), C 3 H 5 OS (m/z89). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 162.0. 2.4.12. 5l: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C = O), 1186.1(N = C): 1 NMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M + ) C 23 H 21 O 7 N 2 S 2 , C 18 H 14 O 2 N 2 S 2 (m/z 354), C 12 H 9 ON 2 S 2 (m/z 261), C 6 H 6 O (m/z 94), C 6 H 6 ON 2 S 2 (m/z 86), C 6 H 6 (m/z 78), C 3 H 3 NS (m/z 85), C 3 H 5 OS (m/z89). 13 C NMR (300 MHz, DMSO- d 6 ) 67.9, 48.2, 54.5, 54.8, 54.4, 54.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.4, 140.4, 162.4. Table 1 Characterization data of compounds 3(a-l). Comp R* Mol Formula RF M. P. (°C) Yield (%) Analysis fond (calcd)% (obs) Value Eluent a C H N S 3a -H C 17 H 14 ON 2 S 2 0.81 128 71 62.5 (62.9) 4.2 (4.7) 8.5 (8.7) 19.6 (19.4) 3b 2-OH C 18 H 14 O 2 N 2 S 2 0.91 137 67 61.01 (61.74) 3.95 (3.4) 7.9 (7.2) 18.0 (18.1) 3c 3-OH C 18 H 14 O 2 N 2 S 2 0.87 131 65 61.01 (61.74) 3.95 (3.4) 7.9 (7.2) 18.0 (18.1) 3d 4-OH C 18 H 14 O 2 N 2 S 2 0.65 130 58 61.01 (61.74) 3.95 (3.4) 7.9 (7.2) 18.0 (18.1) 3e 2-NO 2 C 18 H 12 O 3 N 3 S 2 0.41 148 68 56.8 (56.6) 3.1 (3.6) 11.1 (11.2) 16.8 (16.4) 3f 3-NO 2 C 18 H 12 O 3 N 3 S 2 0.57 144 64 56.8 (56.6) 3.1 (3.6) 11.1 (11.2) 16.8 (16.4) 3g 4-NO 2 C 18 H 12 O 3 N 3 S 2 0.74 147 81 56.8 (56.6) 3.1 (3.6) 11.1 (11.2) 16.8 (16.4) 3h 2-Cl C 18 H 12 ON 2 S 2 Cl 0.52 153 66 37.3 (37.6) 4.7 (4.3) 11.1 (11.2) 25.4 (25.3) 3i 4-Cl C 18 H 12 ON 2 S 2 Cl 0.65 157 74 37.3 (37.6) 4.7 (4.3) 11.1 (11.2) 25.4 (25.3) 3j 2-OCH3 C 18 H 16 O 2 N 3 S 2 0.93 158 66 58.0 (58.6) 4.3 (4.3) 7.3 (7.2) 17.2 (17.8) 3k 4-OCH3 C 18 H 16 O 2 N 3 S 2 0.80 167 77 58.0 (58.6) 4.3 (4.3) 7.3 (7.2) 17.2 (17.8) 3l 3, 4, 5 (OCH 3 ) 3 C 21 H 20 O 5 N 2 S 2 0.45 177 72 56.7 (56.6) 4.5 (4.3) 6.5 (6.4) 14.9 (14.6) *Solvent for crystallization: aq. Ethanol for 3a-i; methanol for 3j-l. a Eluents for TLC: ethyl acetate-acetone (6:4) for 3a, 3b, 3c, 3d, 3f ethyl acetate-acetone (7:3) for 3e, 3g, 3h, 3j, 3k, 3l. Table 2 Characterization data of compounds (4a-l). Comp R Mol Formula RF M. P. (°C) Yield (%) Analysis found (calcd)% (obs) Value Eluent a C H N S 4a -H C 26 H 30 O 7 N 2 S 2 0.72 172 80 57.14 (57.1) 5.2 (5.3) 5.12 (5.7) 11.2 (11.4) 4b 2-OH C 26 H 30 O 8 N 2 S 2 0.53 177 67 55.5 (55.7) 5.3 (5.0) 4.9 (4.2) 11.3 (11.8) 4c 3-OH C 26 H 30 O 8 N 2 S 2 0.45 171 65 55.5 (55.7) 5.3 (5.0) 4.9 (4.2) 11.3 (11.8) 4d 4-OH C 26 H 30 O 8 N 2 S 2 0.92 176 68 55.5 (55.7) 5.3 (5.0) 4.9 (4.2) 11.3 (11.8) 4e 2-NO 2 C 26 H 29 O 9 N 3 S 2 0.45 185 58 52.7 (52.6) 4.4 (4.6) 7.1 (7.2) 10.7 (10.8) 4f 3-NO 2 C 26 H 29 O 9 N 3 S 2 0.43 159 78 52.7 (52.6) 4.4 (4.6) 7.1 (7.2) 10.7 (10.8) 4g 4-NO 2 C 26 H 29 O 9 N 3 S 2 0.65 182 83 52.7 (52.6) 4.4 (4.6) 7.1 (7.2) 10.7 (10.8) 4h 2-Cl C 26 H 30 O 7 N 2 S 2 Cl 2 0.64 173 76 53.5 (53.6) 5.3 (5.3) 4.8 (4.4) 11.0 (11.8) 4i 4-Cl C 26 H 30 O 7 N 2 S 2 Cl 2 0.55 166 75 53.5 (53.6) 5.0 (5.3) 4.8 (4.4) 11.0 (11.8) 4j 2-OCH 3 C 27 H 31 O 8 N 2 S 2 0.47 143 67 56.5 (56.6) 5.3 (5.3) 4.3 (4.2) 11.7 (11.8) 4k 4-OCH 3 C 27 H 31 O 7 N 2 S 2 0.56 173 87 56.5 (56.6) 5.3 (5.3) 4.3 (4.2) 11.7 (11.8) 4l 3, 4, 5 (OCH 3 ) 2 C 29 H 38 O 10 N 2 S 2 0.86 178 78 54.5 (54.6) 5.9 (5.3) 4.3 (4.4) 10.7 (10.8) *Solvent for crystallization: aq. Ethanol for 4a-i; methanol for 4j-l. A Eluents for TLC: ethyl acetate-chloroform(8:2) for 4a, 4b, 4c, 4d, 4f ethyl acetate-acetone (6:4) for 4e, 4g, 4h, 4j, 4k, 4l. Table 3 Characterization data of compounds (5a-l). Comp R* Mol Formula RF M. P. (°C) Yield (%) Analysis found (calcd)% (obs) Value Eluent a C H N S 5a -H C 19 H 15 O 2 N 3 Cl 0.44 197 77 64.77 (64.1) 4.2 (4.3) 11.9 (11.7) 9.7 (9.4) 5b 2-OH C 19 H 16 O 3 N 3 Cl 0.54 187 87 65.76 (65.74) 4.0 (4.0) 16.1 (16.2) 9.7 (9.4) 5c 3-OH C 19 H 16 O 3 N 3 Cl 0.57 176 65 65.76 (65.74) 4.0 (4.0) 16.1 (16.2) 9.7 (9.4) 5d 4-OH C 19 H 16 O 3 N 3 Cl 0.66 176 58 65.76 (65.74) 4.0 (4.0) 16.1 (16.2) 9.7 (9.4) 5e 2-NO 2 C 19 H 15 O 4 N 4 Cl 0.74 181 68 60.7 (60.6) 3.4 (3.6) 18.1 (18.2) 9.7 (9.4) 5f 3-NO 2 C 19 H 15 O 4 N 4 Cl 0.73 189 64 60.7 (60.6) 3.4 (3.6) 18.1 (18.2) 9.7 (9.4) 5g 4-NO 2 C 19 H 15 O 4 N 4 Cl 0.44 184 81 67.5 (67.6) 5.3 (5.1) 18.7 (18.5) 9.7 (9.4) 5h 2-Cl C 18 H 15 O 2 N 3 Cl 2 0.53 183 66 62.5 (62.6) 5.3 (5.3) 15.3 (15.2) 9.7 (9.4) 5i 4-Cl C 18 H 15 O 2 N 3 Cl 2 0.64 168 77 66.5 (66.6) 4.3 (4.3) 15.5 (15.4) 9.7 (9.4) 5j 2-OCH3 C 20 H 18 O 3 N 3 Cl 0.72 183 66 62.5 (62.6) 5.3 (5.3) 15.3 (15.2) 9.7 (9.4) 5k 4-OCH3 C 20 H 18 O 3 N 3 Cl 0.89 187 77 66.5 (66.6) 4.3 (4.3) 15.5 (15.4) 9.7 (9.4) 5l 2-N (CH3)2 C 21 H 21 O 2 N 4 Cl 0.23 170 77 66.5The brominating reagent was combined with 21.6 g of finely (66.6) 4.3 (4.3) 15.5 (15.4) 9.7 (9.4) *Solvent for crystallization: aq. Ethanol for 5a-i; methanol for 5j-l. a Eluents for TLC: ethyl acetate-acetone (7:3) for 5a, 5b, 5c, 5d, 5f ethyl acetate-acetone (6:4) for 5e, 5g, 5h, 5j, 5k, 5l. 3. Biological activities Comparative study of 4-(2-amino-1, 3-thiazol-4-yl) Phenol (1) and compounds 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 3(a-l) , 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 4(a-l) and 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 5(a-l) have been observed by using Norfloxacine and Griseofulvin as standards. The enhancement in biological activity of compound (1) as compared with the newly synthesized 3(a-i) , 4(a-l) , 5(a-l) has been observed. The synthesized compounds were tested at 100 ug/ml concentrations against Escherichia coli , Pseudomonas aeruginosa , Staphylococcus aureus , Proteus vulgaris and fungal cultures such as Aspergillus niger and Candida albicans for its antibacterial and antifungal screening as shown in Tables 4 , 5 , and 6 . Table 4 Data for in vitro antibacterial and anti-fungal activities (in mm) Comp. Minimum inhibitory concentration’s g/ml E. Coli S. aurous Ps. aeruginosa P. Vulgaris A. niger C. albicans 3a 14 15 17 17 14 20 3b 16 10 12 13 24 15 3c 18 12 14 16 15 12 3d 13 9 10 11 17 - 3e 14 12 13 20 12 22 3f 15 11 12 9 11 21 3g 9 12 10 12 12 13 3h NA 10 5 9 8 11 3i 12 10 NA 10 18 12 3j 17 7 12 14 12 NA 3k 14 10 7 8 - 11 3l 12 13 12 10 18 16 NA: not active; -: no inhibition of growth. Table 5 Data for in vitro antibacterial and anti-fungal activities (in mm) Comp. Minimum inhibitory concentration’s g/ml E. Coli S. aurous Ps. aeruginosa P. Vulgaris A. niger C. albicans 4a 14 17 20 14 17 19 4b 15 13 14 15 20 14 4c 17 11 10 12 15 14 4d 13 9 10 11 17 20 4e 14 12 15 13 12 22 4f 15 11 - 9 14 21 4g 13 NA 7 10 13 12 4h 14 15 12 11 13 14 4i 12 14 12 15 18 20 4j 17 14 12 13 16 15 4k 13 10 11 8 22 11 4l 12 NA 14 15 18 13 NA: not active; -: no inhibition of growth. Table 5 Data for in vitro antibacterial and anti-fungal activities (in mm). Comp. Minimum inhibitory concentration’s g/ml E. Coli S. aurous Ps. aeruginosa P. Vulgaris A. niger C. albicans 5a 15 17 20 25 30 35 5b 13 12 15 17 24 30 5c 15 12 - 14 19 20 5d 14 10 11 12 17 18 5e 14 12 13 14 12 22 5f 15 11 10 9 20 21 5g 9 12 7 10 13 12 5h 14 10 5 8 13 11 5i 12 NA 13 10 18 17 5j 17 7 12 14 12 18 5k 14 10 12 13 11 11 5l 12 NA 12 10 18 14 NA: not active; -: no inhibition of growth. 4. Antioxidant activity The proportion of free radical scavenging activity revealed by the test compounds 3a-l, 4a-l and 5a-l was quantified using the 1, 1-diphenyl picryl hydrazyl (DPPH) assay technique. Drug stock solutions with concentrations of 1 mg mL-1 in methanol were diluted to produce final concentrations of 2, 4, 6, 8, and 10 mg mL-1. The findings were read after adding a DPPH methanol solution (1 mL, 0.3 M mol) to 2.5 mL of drug solutions with different concentrations and letting the mixture react at room temperature. The proportion of antioxidant activity was determined from the observations made after 30 minutes of observation by measuring the absorbance values at 518 nm. Methanol was applied as the solvent, while ascorbic acid was used as the reference. The estimated percentage of inhibition based on concentration is shown in Fig. 4 . The outcomes are shown in Table 6 . Ascorbic acid was the usual medication. 5. Result and discursion Considering the pharmacological properties of thaizolidine, thourea, and 4-hydroxyacetophenone in ethanol as previously described, 4-(2-amino-1, 3-thiazol-4-yl) is formed as the starting material. After combining various aldehydes and stirring for six hours, phenol (1) was transformed into 4-(2-schiffs base-1, 3-thiazol-4-yl) phenol (2) was then undergo cyclisation in presence of glacial acetic acid gives 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 3 (a-l) and a-D-2, 3, 4, 6-tetra- O -acetyl Glucopyranosyl bromide were dissolved in dioxane at 100 0 C and kept at this temperature for 4 hours to give 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 4 (a-l) and 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 5 (a-l) . Among the series of compounds created, compounds 3(a-l), 4(a-l), and 5(a-l) with (hydroxyl phenyl, nitro phenyl, chlorophenyl, methoxyphenyl, and N (di-methylphenyl) have demonstrated good antioxidant activity. In order to find a possible pharmacophore, these chemicals will therefore be further investigated for their antibacterial properties. 6. Conclusion The findings of this investigation show that the current O-(β -D-Glucopyranosyl) synthetic approach is a straightforward, effective, affordable, and simple way to synthesize molecules with biological activity 3-[4-(phenyl-4-hydroxy)3-thiazole-2-yl] --2-phenyl-1, 3-thiazolidin-4-one 3(a-l), 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 4(a-l) and 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 5(a-l) . Compared to basic Thaizolidine, these compounds demonstrated good performance at concentrations of 100 ug/ml against a variety of bacteria and viruses, including Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Proteus vulgaris, and fungal cultures including Aspergillus niger and Candida albicans. The compounds 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 3(a-l) , 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 4(a-l) and 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 5(a-l) have shown good antioxidant activity. Declarations Declaration of competing interest The authors affirm that they have no financial stake in the outcome of the work described in the publication. Supplementary data Supplementary data to this manuscript can be found online. Competing Interests The findings of this investigation show that the current O-(β -D-Glucopyranosyl) synthetic approach is a straightforward, effective, affordable, and simple way to synthesize molecules with biological activity 3-[4-(phenyl-4-hydroxy)3-thiazole-2-yl] --2-phenyl-1, 3-thiazolidin-4-one 3(a-l), 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 4(a-l) and 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 5(a-l). Compared to basic Thaizolidine, these compounds demonstrated good performance at concentrations of 100 ug/ml against a variety of bacteria and viruses, including Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Proteus vulgaris, and fungal cultures including Aspergillus niger and Candida albicans. Author Contribution There is no any conflict of inference in Synthesis of 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one, Chanda W. Awaghade1prepared figures 1-3, Meghasham N. Narule*wrote the main manuscript text , Niren Kathale1, 1Department of Chemistry, Sardar Patel Mahavidyalaya, Chandrapur. Department of Chemistry, Vidya Vikas Arts, Commerce & Science College, Samudrapur, Dist-Wardha, 442305, INDIA. All authors reviewed the manuscript Acknowledgement The Director SAIF Punjab University Chandigarh is thanked by the author for supplying spectral and analytical data. Data availability Data will be made available on request. References Ostrovskii, V.A.; Koldobskii, G.I.; Trifonov, R.E. Tetrazoles. In Comprehensive Heterocyclic Chemistry III;Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., Taylor, R.J.K., Eds.; Elsevier: Oxford, UK, 2008; Volume 6,pp. 257–423. Couri, M.R.; Luduvico, I.; Santos, L.; Alves, R.; Prado, M.A.; Gil, R.F. 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Table 6 Table 6 is available in the Supplementary Files section. scheme 1 Scheme 1 is available in the Supplementary Files section. Additional Declarations Competing interest reported. The findings of this investigation show that the current O-(β -D-Glucopyranosyl) synthetic approach is a straightforward, effective, affordable, and simple way to synthesize molecules with biological activity 3-[4-(phenyl-4-hydroxy)3-thiazole-2-yl] --2-phenyl-1, 3-thiazolidin-4-one 3(a-l), 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 4(a-l) and 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 5(a-l). Compared to basic Thaizolidine, these compounds demonstrated good performance at concentrations of 100 ug/ml against a variety of bacteria and viruses, including Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Proteus vulgaris, and fungal cultures including Aspergillus niger and Candida albicans. Supplementary Files Suplimentarydata.docx Table6.docx Scheme1.png Scheme 1-Reaction scheme1 Cite Share Download PDF Status: Posted Version 1 posted You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. Our growing team is made up of researchers and industry professionals working together to solve the most critical problems facing scientific publishing. Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-5317015","acceptedTermsAndConditions":true,"allowDirectSubmit":true,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":369807435,"identity":"f4ef1d13-a2e8-42e9-b46f-1b85ab989677","order_by":0,"name":"Chanda W. Awaghade","email":"","orcid":"","institution":"Vidya Vikas Arts, Commerce \u0026 Science College","correspondingAuthor":false,"prefix":"","firstName":"Chanda","middleName":"W.","lastName":"Awaghade","suffix":""},{"id":369807436,"identity":"1e0f90f1-b1bc-4cc8-94ca-a2c13e107aad","order_by":1,"name":"Meghasham N. Narule (corresponding Author)","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAABEUlEQVRIiWNgGAWjYHACNiA+AGIwPmBgYOZhbwZyEgqI08JsANLCcywBqMWAOC1sEkAtDGAtDHi06La3X3vw488ded0G3mPVFRXWMjxs3IkfHhgwyPOLHcCqxezMmXLD3rZnhtsO8KXdPHMmnYeHjXezBNBhhjNnJ2DXciMnTYK34TDjtgM8Zjcb2w7z2Mv3bgBpSTC4jUPL/Tdpkn/+HLYHaSls/HcYbMsPvFpusB+T5mE7nAjSwtjYANayDb8tZ3LYpGXbDicDtRhLNhwD+2WbRYKBBG6/HD/+TPLNn8O2QC2GHxtqrO1BDrv5o8JGnl8auxYGBh5oFMg/QBGWwKEcBNgf4JEcBaNgFIyCUQAEAGWnYF5iwYrsAAAAAElFTkSuQmCC","orcid":"","institution":"Vidya Vikas Arts, Commerce \u0026 Science College","correspondingAuthor":true,"prefix":"","firstName":"Meghasham","middleName":"N. Narule (corresponding","lastName":"Author)","suffix":""},{"id":369807437,"identity":"5ef6d9d1-fdd2-463c-9ab0-fd5db9b60144","order_by":2,"name":"Niren Kathale","email":"","orcid":"","institution":"Vidya Vikas Arts, Commerce \u0026 Science College","correspondingAuthor":false,"prefix":"","firstName":"Niren","middleName":"","lastName":"Kathale","suffix":""}],"badges":[],"createdAt":"2024-10-23 08:23:05","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-5317015/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-5317015/v1","draftVersion":[],"editorialEvents":[],"editorialNote":"","failedWorkflow":false,"files":[{"id":68244087,"identity":"55ed228a-b82b-4b99-bdba-26747cc97ae2","added_by":"auto","created_at":"2024-11-05 08:52:55","extension":"png","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":30446,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eBiological activity of the compounds 3(a-l).\u003c/strong\u003e\u003c/p\u003e","description":"","filename":"1.png","url":"https://assets-eu.researchsquare.com/files/rs-5317015/v1/a7e525d5ec30c29b063e364a.png"},{"id":68245816,"identity":"d4ea3ce7-8e62-460b-960e-2c0e45566fb5","added_by":"auto","created_at":"2024-11-05 09:08:55","extension":"png","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":17909,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eBiological activity of the compounds 4(a-l).\u003c/strong\u003e\u003c/p\u003e","description":"","filename":"2.png","url":"https://assets-eu.researchsquare.com/files/rs-5317015/v1/65a69e2b56f372ab75ed647b.png"},{"id":68245043,"identity":"df902a36-af87-4eaa-b67e-26d823f43baf","added_by":"auto","created_at":"2024-11-05 09:00:55","extension":"png","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":21823,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eBiological activity of the compounds 5(a-l).\u003c/strong\u003e\u003c/p\u003e","description":"","filename":"3.png","url":"https://assets-eu.researchsquare.com/files/rs-5317015/v1/b8d32d1d141be5298465d73e.png"},{"id":68244089,"identity":"a0840da7-6e74-473b-b3e6-3d29e27e9adc","added_by":"auto","created_at":"2024-11-05 08:52:55","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":12855,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eAntioxidant activity of compounds 3(a-l), 4(a-l) and 5(a-I).\u003c/strong\u003e\u003c/p\u003e","description":"","filename":"4.png","url":"https://assets-eu.researchsquare.com/files/rs-5317015/v1/2b0bc1d35d0e06422dc09b19.png"},{"id":68800561,"identity":"37331c5f-2051-4df2-ad56-6c70c10c0f7a","added_by":"auto","created_at":"2024-11-12 07:17:13","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":2235971,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-5317015/v1/5af6920f-db5d-44b1-a3de-3217f6f7f42a.pdf"},{"id":68244090,"identity":"930eb7d4-81d8-4621-b07c-e9efc98f0c72","added_by":"auto","created_at":"2024-11-05 08:52:55","extension":"docx","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":139930,"visible":true,"origin":"","legend":"","description":"","filename":"Suplimentarydata.docx","url":"https://assets-eu.researchsquare.com/files/rs-5317015/v1/f8a6de12d3e1d6f44a26fd41.docx"},{"id":68244088,"identity":"d5d04fb5-dbc4-4114-baae-3b14e3c96875","added_by":"auto","created_at":"2024-11-05 08:52:55","extension":"docx","order_by":2,"title":"","display":"","copyAsset":false,"role":"supplement","size":18027,"visible":true,"origin":"","legend":"","description":"","filename":"Table6.docx","url":"https://assets-eu.researchsquare.com/files/rs-5317015/v1/c689d8619feebcae2beb2528.docx"},{"id":68244086,"identity":"20e4a641-316b-487d-8a41-b466ddf6835b","added_by":"auto","created_at":"2024-11-05 08:52:55","extension":"png","order_by":3,"title":"","display":"","copyAsset":false,"role":"supplement","size":25160,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eScheme 1-Reaction scheme1\u003c/strong\u003e\u003c/p\u003e","description":"","filename":"Scheme1.png","url":"https://assets-eu.researchsquare.com/files/rs-5317015/v1/4a6fcaa0cdde80c09d657fa4.png"}],"financialInterests":"Competing interest reported. The findings of this investigation show that the current O-(β -D-Glucopyranosyl) synthetic approach is a straightforward, effective, affordable, and simple way to synthesize molecules with biological activity 3-[4-(phenyl-4-hydroxy)3-thiazole-2-yl] --2-phenyl-1, 3-thiazolidin-4-one 3(a-l), 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 4(a-l) and 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 5(a-l). Compared to basic Thaizolidine, these compounds demonstrated good performance at concentrations of 100 ug/ml against a variety of bacteria and viruses, including Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Proteus vulgaris, and fungal cultures including Aspergillus niger and Candida albicans.","formattedTitle":"Synthesis of novel 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one as antioxidant agent","fulltext":[{"header":"1. Introduction","content":"\u003cp\u003eDue to their wide range of pharmacological effects, numerous O-(β -D-Glucopyranosyl)-4-Thiazolidinones have attracted more attention in the current year's synthesis. These heterocyclic compounds belong to an important class. This effort aims to explore the chemistry of O-(β-D-Glucopyranosyl)-4-Thiazolidinones by synthesizing significant amounts of the compound in a lab setting using both classical and microwave analysis. Known by many other names, heterocyclic compounds are organic chemical compounds with one or more heteroatoms arranged in a ring-like shape. Heterocyclic can be both cyclic and acyclic \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e \u0026ndash; \u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e14\u003c/span\u003e\u003c/sup\u003e. The general structure of heterocyclic is similar to that of cyclic organic compounds, which have only carbon atom in their structure, but the substitute of one or more carbon atoms by heteroatoms gives heterocyclic physico-chemical properties that are distinct from those of all carbon ring analogs\u003csup\u003e\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e \u0026ndash; \u003cspan citationid=\"CR17\" class=\"CitationRef\"\u003e17\u003c/span\u003e\u003c/sup\u003e. Heterocyclic involve a wide range of uses, including agrochemical, medicinal, and veterinary\u003csup\u003e\u003cspan citationid=\"CR18\" class=\"CitationRef\"\u003e18\u003c/span\u003e\u003c/sup\u003e. Such compounds are also used in sanitizers, antioxidants, copolymers, corrosion inhibitors, dyestuff\u003csup\u003e\u003cspan citationid=\"CR19\" class=\"CitationRef\"\u003e19\u003c/span\u003e\u003c/sup\u003e, etc. Heterocyclic are currently employed in the production of a wide range of organic chemical substances\u003csup\u003e\u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e20\u003c/span\u003e\u003c/sup\u003e. Heterocyclic components are found in a number of substances, the majority of which are found in nature. These include morphine, vinblastine, reserpine, alkaloids, and several antibiotics, including cephalosporin and penicillin. The antibacterial activity of schiff bases makes them significant, and their stability and chelating qualities make them exceptional \u003csup\u003e\u003cspan citationid=\"CR21\" class=\"CitationRef\"\u003e21\u003c/span\u003e\u003c/sup\u003e. It is possible to produce innovative medications using schiff bases. Chemists are interested in Schiff base complexes with metal ions because imines have been used for their antiviral, antituberculosis, antibacterial, antifungal, and antimalarial properties \u003csup\u003e\u003cspan citationid=\"CR22\" class=\"CitationRef\"\u003e22\u003c/span\u003e\u003c/sup\u003e. Schiff bases and their metal complexes contain halogens that display antimicrobial activity \u003csup\u003e\u003cspan citationid=\"CR23\" class=\"CitationRef\"\u003e23\u003c/span\u003e\u003c/sup\u003e.4-thiazolidinones have reported for their antibacterial, antiparkinsonian and anti-convalescent activities\u003csup\u003e\u003cspan citationid=\"CR24\" class=\"CitationRef\"\u003e24\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR25\" class=\"CitationRef\"\u003e25\u003c/span\u003e\u003c/sup\u003e. 4-thiazolidinones find their application as local anesthetics and also as moderate tuberculosis agent. Applications of thiazolidinones, a significant class of heterocyclic chemicals, in medicine have been extensively studied. Numerous biological processes\u003csup\u003e\u003cspan additionalcitationids=\"CR27 CR28 CR29 CR30 CR31 CR32 CR33 CR34 CR35 CR36 CR37 CR38 CR39 CR40 CR41 CR42 CR43 CR44 CR45 CR46\" citationid=\"CR26\" class=\"CitationRef\"\u003e26\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR47\" class=\"CitationRef\"\u003e47\u003c/span\u003e\u003c/sup\u003e, including signaling, cell-cell communication, molecular and cellular targeting, and hormone production are among the numerous significant types of substances that glycosides constitute. Other glycoside-containing molecules include sweeteners, alkaloids, flavonoids, vitamins, antibiotics and sweeteners.\u003c/p\u003e\u003cp\u003e\u003cstrong\u003eScheme 1\u003c/strong\u003e outlines the series of reactions that result in the creation of desired heterocyclic compounds. In ethanol, thiourea and 4-hydroxyacetophenone combine to generate 4-(2-amino-1, 3-thiazol-4-yl) as the starting material. To create 4-(2-schiffs base), phenol (1) was produced by stirring it with various aldehydes for six hours.-1, 3-thiazol-4-yl After that, phenol (2) underwent cyclization in the presence of glacial acetic acid, producing 3-[4-thiazole-2-yl, 4-(4-hydroxy phenyl)-1]\u0026alpha;-D-2, 3, 4, 6-tetra-O-acetyl Glucopyranosyl bromide and 3-thiazolidin-4-one (3) were dissolved in dioxane at 1000C and maintained at this temperature for 4 hours to yield 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- \u0026beta;- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl] and 3-thiazolidin-4-one (3).3-thiazolidin-4-one, 2-phenyl-1 (4).In a 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- \u0026beta;- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl] solutionthree-thiazolidin-4-one and two-phenyl-1 (4) Newly made 5% sodium methoxide solution was added to 25 mL of dry methanol, and the mixture was allowed to sit at room temperature for 24 hours to yield 3-[4-(4- O-(\u0026beta; -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one (5).\u003c/p\u003e"},{"header":"2. Experimental","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003e2.1 Materials and methods\u003c/h2\u003e \u003cp\u003eUsing an open capillary tube, the melting points were ascertained, and the results were unchanged. KBr pellets' infrared spectra were captured with a Perkin-Elmer spectrophotometer model 157. The Bruker-300 Varian MHz FT NMR spectrometer was used to record 1H NMR spectra in either CDCl3 or DMSO. TMS was used as the internal standard. Iodine vapors were used to pinpoint the spots, and thin-layer chromatography (TLC) on silica gel G plates was used to evaluate the chemicals' purity. Information on the compounds' characteristics is provided in Tables\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e and \u003cspan refid=\"Tab4\" class=\"InternalRef\"\u003e4\u003c/span\u003e.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec4\" class=\"Section2\"\u003e \u003ch2\u003e2.2 Synthesis starting material\u003c/h2\u003e \u003cdiv id=\"Sec5\" class=\"Section3\"\u003e \u003ch2\u003e2.2.1 4-(2-amino-1, 3-thiazol-4-yl) Phenol\u003c/h2\u003e \u003cp\u003eCompound (1) was prepared by gradually adding a cold solution of 4-hydroxyacetophenone (0.01 mol) to a thiourea solution (0.01 mol) in ethanol while stirring the mixture continuously (0.01 mol). The reaction mixtures were stirred for a further four hours. Distillation was used to remove the solvent, and the residue was dried, cleaned with petroleum ether, and crystallized from ethanol. Yield 70%:M.P.213\u003csup\u003e0\u003c/sup\u003eC: IR (KBr):3249 (OH), 3153(NH\u003csub\u003e2\u003c/sub\u003e), 1595(ArH), (C-S-C), (N\u0026thinsp;=\u0026thinsp;C): 1NMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), (1H, s, ArH).\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec6\" class=\"Section3\"\u003e \u003ch2\u003e2.2.2 Synthesis of 4-(2-schiffs base-1, 3-thiazol-4-yl) Phenol\u003c/h2\u003e \u003cp\u003e4-(2-amino-1, 3-thiazol-4-yl) Phenol (1) (0.01mole) and various aldehydes (0.01mole) in methanol were agitated for 6 hours, and the resulting solid was cleaned with ether, dried, and crystallized from ethanol. The reaction liquid was then poured over crushed ice. Yield 70%:M.P.213\u003csup\u003e0\u003c/sup\u003eC: IR (KBr):3249 (OH), 3153(NH\u003csub\u003e2\u003c/sub\u003e), 1595(ArH), (C-S-C), (N\u0026thinsp;=\u0026thinsp;C): 1NMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), (1H, s, ArH).\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec7\" class=\"Section3\"\u003e \u003ch2\u003e2.2.3. 3a: Synthesis of 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003cp\u003eCompound 3 (0.01 Mole) is cyclized in 100% ethanol, and a few drops of glacial acetic acid are also added to the experiment. After being stirred for six to seven hours, the reaction liquid was poured over crushed ice. The resulting solid was then dried, washed with ether, and crystallized from ethanol. Yield 71%:M.P.128\u003csup\u003e0\u003c/sup\u003eC: IR (KBr):3143.8 (OH), 2808.2(N\u0026thinsp;=\u0026thinsp;C), 1596.9(ArH), 1508.2(C-S-C), 1444.6(C-C), 1645.2(C\u0026thinsp;=\u0026thinsp;O), 1232.4(C-N-C), 1278.7(C-S-C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), 7.2\u0026ndash;7.1(1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec8\" class=\"Section3\"\u003e \u003ch2\u003e2.2.4. 3b: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003cp\u003eIR (KBr):3141.2 (OH), 2818.1(N\u0026thinsp;=\u0026thinsp;C), 1592.9(ArH), 1511.2(C-S-C), 1444.6(C-C), 1645.2(C\u0026thinsp;=\u0026thinsp;O), 1232.4(C-N-C), 1278.7(C-S-C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), 7.2\u0026ndash;7.1(1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec9\" class=\"Section3\"\u003e \u003ch2\u003e2.2.5. 3c: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003cp\u003eIR (KBr):3143.5 (OH), 2808.4(N\u0026thinsp;=\u0026thinsp;C), 1596.9(ArH), 1528.2(C-S-C), 1442.6(C-C), 1645.2(C\u0026thinsp;=\u0026thinsp;O), 1232.4(C-N-C), 1278.7(C-S-C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), 7.2\u0026ndash;7.1(1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec10\" class=\"Section3\"\u003e \u003ch2\u003e2.2.6. 3d: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003cp\u003eIR (KBr):3133.8 (OH), 2828.2(N\u0026thinsp;=\u0026thinsp;C), 1596.9(ArH), 1538.2(C-S-C), 1434.6(C-C), 1641.2(C\u0026thinsp;=\u0026thinsp;O), 1232.4(C-N-C), 1278.7(C-S-C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), 7.2\u0026ndash;7.1(1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec11\" class=\"Section3\"\u003e \u003ch2\u003e2.2.7. 3e: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003cp\u003eIR (KBr):3043.8 (OH), 2708.2(N\u0026thinsp;=\u0026thinsp;C), 1593.9(ArH), 1558.2(C-S-C), 1445.6(C-C), 1645.2(C\u0026thinsp;=\u0026thinsp;O), 1232.4(C-N-C), 1278.7(C-S-C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), 7.2\u0026ndash;7.1(1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec12\" class=\"Section3\"\u003e \u003ch2\u003e2.2.8. 3f: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003cp\u003eIR (KBr):3143.2 (OH), 2808.1(N\u0026thinsp;=\u0026thinsp;C), 1596.2(ArH), 1508.1(C-S-C), 1444.1(C-C), 1645.3(C\u0026thinsp;=\u0026thinsp;O), 1232.4(C-N-C), 1278.7(C-S-C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), 7.2\u0026ndash;7.1(1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec13\" class=\"Section3\"\u003e \u003ch2\u003e2.2.9. 3g: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003cp\u003eIR (KBr):3153.8 (OH), 2858.2(N\u0026thinsp;=\u0026thinsp;C), 1595.9(ArH), 1508.5(C-S-C), 1444.5(C-C), 1645.5(C\u0026thinsp;=\u0026thinsp;O), 1232.4(C-N-C), 1278.7(C-S-C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), 7.2\u0026ndash;7.1(1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec14\" class=\"Section3\"\u003e \u003ch2\u003e2.2.10. 3h: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003cp\u003eIR (KBr):3123.8 (OH), 2828.2(N\u0026thinsp;=\u0026thinsp;C), 1526.9(ArH), 1528.2(C-S-C), 1444.6(C-C), 1645.2(C\u0026thinsp;=\u0026thinsp;O), 1232.4(C-N-C), 1278.7(C-S-C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), 7.2\u0026ndash;7.1(1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec15\" class=\"Section3\"\u003e \u003ch2\u003e2.2.11. 3i: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003cp\u003eIR (KBr):3143.8 (OH), 2808.2(N\u0026thinsp;=\u0026thinsp;C), 1526.9(ArH), 1528.2(C-S-C), 1444.6(C-C), 1625.2(C\u0026thinsp;=\u0026thinsp;O), 1222.4(C-N-C), 1278.7(C-S-C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), 7.2\u0026ndash;7.1(1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 50.2, 52.1, 54.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec16\" class=\"Section3\"\u003e \u003ch2\u003e2.2.12. 3j: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003cp\u003eIR (KBr):3143.8 (OH), 2808.2(N\u0026thinsp;=\u0026thinsp;C), 1596.9(ArH), 1508.2(C-S-C), 1444.6(C-C), 1645.2(C\u0026thinsp;=\u0026thinsp;O), 1232.4(C-N-C), 1278.7(C-S-C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), 7.2\u0026ndash;7.1(1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 50.1, 52.2, 54.3. 79.4, 74.4, 114.5, 148.5, 126.5, 147.4, 152.5.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec17\" class=\"Section3\"\u003e \u003ch2\u003e2.2.13. 3k: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003cp\u003eIR (KBr):3143.8 (OH), 2808.2(N\u0026thinsp;=\u0026thinsp;C), 1596.9(ArH), 1508.2(C-S-C), 1444.6(C-C), 1645.2(C\u0026thinsp;=\u0026thinsp;O), 1232.4(C-N-C), 1278.7(C-S-C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), 7.2\u0026ndash;7.1(1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 57.2, 57.1, 55.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec18\" class=\"Section3\"\u003e \u003ch2\u003e2.2.14. 3l: 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003cp\u003eIR (KBr):3143.8 (OH), 2808.2(N\u0026thinsp;=\u0026thinsp;C), 1596.9(ArH), 1508.2(C-S-C), 1444.6(C-C), 1645.2(C\u0026thinsp;=\u0026thinsp;O), 1232.4(C-N-C), 1278.7(C-S-C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), 7.2\u0026ndash;7.1(1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 59.2, 58.1, 547.3. 79.2, 74.2, 114.4, 148.5, 126.6, 147.4, 152.0.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec19\" class=\"Section3\"\u003e \u003ch2\u003e2.3.1. 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003c/div\u003e \u003cdiv id=\"Sec20\" class=\"Section3\"\u003e \u003ch2\u003e2.3.2. Brominating reagent\u003c/h2\u003e \u003cp\u003eA 100 mL conical flask was filled with 30 mL of glacial acetic acid, to which 7 mL of molecular bromine was added gradually while the flask was continuously shaken and cooled. For around fifteen minutes, the resulting mixture was let to stand at room temperature. After that, it passed through the glass wool filter.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec21\" class=\"Section3\"\u003e \u003ch2\u003e2.3.3. 2, 3, 4, 6-Tetra-\u003cem\u003eO\u003c/em\u003e-acetyl-a-D-glucopyranosyl bromide\u003c/h2\u003e \u003cp\u003eThe brominating reagent was combined with 21.6 g of finely ground glucose pent acetate. The contents of the flask were allowed to settle at room temperature for two hours following the addition. After adding 30 mL of chloroform to the reaction mixture, it was vigorously agitated for approximately 15 minutes. After then, the mixture was put into ice-cold water. The coating of chloroform was removed. It was cleaned multiple times using aqueous sodium bicarbonate to get rid of extra chloric acid, then again with water and sodium metabisulphite to get rid of extra bromine. After that, the layer of chloroform was dried on top of anhydrous calcium chloride. The solvent was then eliminated using vacuum distillation. After distillation, the thick, oily liquid was repeatedly boiled in petroleum ether to produce tetra-O-acetyl-α-D-glucopyranosyl bromide as a solid. Diethyl ether crystallized into it. Yield 15g, M. P. 88\u003csup\u003e0\u003c/sup\u003eC, [a] \u003csup\u003e\u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e20\u003c/span\u003e\u003c/sup\u003e \u003csub\u003eD\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;+\u0026thinsp;197.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec22\" class=\"Section3\"\u003e \u003ch2\u003e2.3.4. 4a: 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003cp\u003e3-[4-(phenyl-4-hydroxy)3-thiazole-2-yl, -1]Dioxane (40 mL) was used to dissolve \u0026minus;\u0026thinsp;2-phenyl-1, 3-thiazolidin-4-one (0.02 Mol) and a-D-2, 3, 4, 6-tetra-O-acetyl Glucopyranosyl bromide (0.02 Mole) at 1000C. The mixture was then maintained at this temperature for four hours. TLC keeps track of the reaction's progress. Lower pressure was used to extract the solvent. After being dissolved in MeOH-CHCl3 (1:4), the resultant brown syrup was chromatographed on silica gels with a mesh size of 60\u0026ndash;120 and eluted with 10% methanol in chloroform. The brown syrup of 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one was obtained. Yield 80%:M.P.172\u003csup\u003e0\u003c/sup\u003eC: IR (KBr):3249 (OH), 3153(NH\u003csub\u003e2\u003c/sub\u003e), 1595(ArH), (C-S-C), (C-C), (C\u0026thinsp;=\u0026thinsp;O), (N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), (1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 162.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.3.5. 4b: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3249 (OH), 3153(NH\u003csub\u003e2\u003c/sub\u003e), 1595(ArH), (C-S-C), (C-C), (C\u0026thinsp;=\u0026thinsp;O), (N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), (1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 162.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.3.6. 4c: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3249 (OH), 3153(NH\u003csub\u003e2\u003c/sub\u003e), 1595(ArH), (C-S-C), (C-C), (C\u0026thinsp;=\u0026thinsp;O), (N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), (1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.3, 48.2, 57.3, 59.8, 50.4, 53.3, 53.6. 73.2, 77.2, 131.4, 120.5, 136.6, 140.4, 163.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.3.7. 4d: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3249 (OH), 3153(NH\u003csub\u003e2\u003c/sub\u003e), 1595(ArH), (C-S-C), (C-C), (C\u0026thinsp;=\u0026thinsp;O), (N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), (1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 131.4, 120.5, 123.6, 130.4, 162.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.3.8. 4e: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3249 (OH), 3153(NH\u003csub\u003e2\u003c/sub\u003e), 1595(ArH), (C-S-C), (C-C), (C\u0026thinsp;=\u0026thinsp;O), (N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), (1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 127.6, 147.4, 167.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.3.9. 4f: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3249 (OH), 3153(NH\u003csub\u003e2\u003c/sub\u003e), 1595(ArH), (C-S-C), (C-C), (C\u0026thinsp;=\u0026thinsp;O), (N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), (1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 47.2, 57.5, 57.8, 57.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 167.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.3.10. 4g: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3249 (OH), 3153(NH\u003csub\u003e2\u003c/sub\u003e), 1595(ArH), (C-S-C), (C-C), (C\u0026thinsp;=\u0026thinsp;O), (N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), (1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 57.8, 50.4, 52.3, 57.6. 77.2, 77.2, 111.4, 127.5, 126.6, 140.4, 162.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.3.11. 4h: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3249 (OH), 3153(NH\u003csub\u003e2\u003c/sub\u003e), 1595(ArH), (C-S-C), (C-C), (C\u0026thinsp;=\u0026thinsp;O), (N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), (1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.8, 140.4, 162.8.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.3.12. 4i: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3249 (OH), 3153(NH\u003csub\u003e2\u003c/sub\u003e), 1595(ArH), (C-S-C), (C-C), (C\u0026thinsp;=\u0026thinsp;O), (N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), (1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.9, 52.9, 53.9. 77.9, 77.2, 191.4, 120.5, 126.6, 140.4, 162.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.3.13. 4j: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3249 (OH), 3153(NH\u003csub\u003e2\u003c/sub\u003e), 1595(ArH), (C-S-C), (C-C), (C\u0026thinsp;=\u0026thinsp;O), (N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), (1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 73.2, 73.2, 131.4, 120.5, 126.6, 140.4, 162.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.3.14. 4k: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3249 (OH), 3153(NH\u003csub\u003e2\u003c/sub\u003e), 1595(ArH), (C-S-C), (C-C), (C\u0026thinsp;=\u0026thinsp;O), (N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), (1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 162.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.3.15. 4l: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3249 (OH), 3153(NH\u003csub\u003e2\u003c/sub\u003e), 1595(ArH), (C-S-C), (C-C), (C\u0026thinsp;=\u0026thinsp;O), (N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 8.7\u0026ndash;8.9(4H, s, ArH), 7.4\u0026ndash;7.5(5H, s, ArH), (1H, s, OH). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 54.5, 54.8, 54.4, 54.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.4, 140.4, 162.4.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec23\" class=\"Section3\"\u003e \u003ch2\u003e2.4.1. 5a: 2, 3, 5. 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/h2\u003e \u003cp\u003eTo a solution of 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one (0.002 Mole) in 25 mL of dry methanol was added freshly prepared 5% sodium methoxide (1.5 mL) solution and the mixture was kept at room temperature for 24 hour. To produce thick, very hygroscopic dark syrup, the reaction mixture was neutralized using ion-exchange resin (Amberlite IR120, Sdfine H\u0026thinsp;+\u0026thinsp;form), filtered, and concentrated in vacuo. Yield 77%:M.P.197\u003csup\u003e0\u003c/sup\u003eC: IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C\u0026thinsp;=\u0026thinsp;O), 1186.1(N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M\u003csup\u003e+\u003c/sup\u003e) C\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e, C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 354), C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 261), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eO (m/z 94), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 86), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e (m/z 78), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e3\u003c/sub\u003eNS (m/z 85), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eOS (m/z89).\u003csup\u003e13\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 162.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.4.2. 5b: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C\u0026thinsp;=\u0026thinsp;O), 1186.1(N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M\u003csup\u003e+\u003c/sup\u003e) C\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e, C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 354), C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 261), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eO (m/z 94), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 86), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e (m/z 78), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e3\u003c/sub\u003eNS (m/z 85), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eOS (m/z89).\u003csup\u003e13\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 162.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.4.3. 5c: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C\u0026thinsp;=\u0026thinsp;O), 1186.1(N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M\u003csup\u003e+\u003c/sup\u003e) C\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e, C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 354), C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 261), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eO (m/z 94), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 86), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e (m/z 78), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e3\u003c/sub\u003eNS (m/z 85), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eOS (m/z89).\u003csup\u003e13\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.3, 48.2, 57.3, 59.8, 50.4, 53.3, 53.6. 73.2, 77.2, 131.4, 120.5, 136.6, 140.4, 163.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.4.4. 5d: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C\u0026thinsp;=\u0026thinsp;O), 1186.1(N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M\u003csup\u003e+\u003c/sup\u003e) C\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e, C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 354), C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 261), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eO (m/z 94), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 86), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e (m/z 78), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e3\u003c/sub\u003eNS (m/z 85), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eOS (m/z89).\u003csup\u003e13\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 131.4, 120.5, 123.6, 130.4, 162.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.4.5. 5e: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C\u0026thinsp;=\u0026thinsp;O), 1186.1(N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M\u003csup\u003e+\u003c/sup\u003e) C\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e, C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 354), C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 261), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eO (m/z 94), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 86), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e (m/z 78), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e3\u003c/sub\u003eNS (m/z 85), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eOS (m/z89). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 127.6, 147.4, 167.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.4.6. 5f: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C\u0026thinsp;=\u0026thinsp;O), 1186.1(N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M\u003csup\u003e+\u003c/sup\u003e) C\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e, C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 354), C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 261), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eO (m/z 94), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 86), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e (m/z 78), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e3\u003c/sub\u003eNS (m/z 85), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eOS (m/z89). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 47.2, 57.5, 57.8, 57.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 167.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.4.7. 5g: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C\u0026thinsp;=\u0026thinsp;O), 1186.1(N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M\u003csup\u003e+\u003c/sup\u003e) C\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e, C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 354), C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 261), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eO (m/z 94), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 86), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e (m/z 78), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e3\u003c/sub\u003eNS (m/z 85), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eOS (m/z89). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 57.8, 50.4, 52.3, 57.6. 77.2, 77.2, 111.4, 127.5, 126.6, 140.4, 162.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.4.8. 5h: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C\u0026thinsp;=\u0026thinsp;O), 1186.1(N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M\u003csup\u003e+\u003c/sup\u003e) C\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e, C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 354), C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 261), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eO (m/z 94), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 86), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e (m/z 78), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e3\u003c/sub\u003eNS (m/z 85), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eOS (m/z89). \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.8, 140.4, 162.8.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.4.9. 5i: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C\u0026thinsp;=\u0026thinsp;O), 1186.1(N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M\u003csup\u003e+\u003c/sup\u003e) C\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e, C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 354), C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 261), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eO (m/z 94), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 86), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e (m/z 78), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e3\u003c/sub\u003eNS (m/z 85), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eOS (m/z89).\u003csup\u003e13\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.9, 52.9, 53.9. 77.9, 77.2, 191.4, 120.5, 126.6, 140.4, 162.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.4.10. 5j: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C\u0026thinsp;=\u0026thinsp;O), 1186.1(N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M\u003csup\u003e+\u003c/sup\u003e) C\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e, C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 354), C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 261), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eO (m/z 94), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 86), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e (m/z 78), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e3\u003c/sub\u003eNS (m/z 85), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eOS (m/z89).\u003csup\u003e13\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 73.2, 73.2, 131.4, 120.5, 126.6, 140.4, 162.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.4.11. 5k: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C\u0026thinsp;=\u0026thinsp;O), 1186.1(N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M\u003csup\u003e+\u003c/sup\u003e) C\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e, C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 354), C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 261), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eO (m/z 94), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 86), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e (m/z 78), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e3\u003c/sub\u003eNS (m/z 85), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eOS (m/z89).\u003csup\u003e13\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 57.5, 59.8, 50.4, 52.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.6, 140.4, 162.0.\u003c/p\u003e \u003cp\u003e \u003cb\u003e2.4.12. 5l: 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one\u003c/b\u003e IR (KBr):3406.1(OH of glycone moiety), 2929.7(CH-glycone), 2856.4 (CH-thiazole), 1691.5 (ArH), 1569.9(C-S-C), 1448.4(C-C), 1413.7(C\u0026thinsp;=\u0026thinsp;O), 1186.1(N\u0026thinsp;=\u0026thinsp;C): \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eNMR (300 MHz DMSO) d 7.9(4H, s, HO of glucone), 7.03(4H, s, CH), 6.87(1H, s, CH-Thiazole). FAB-MS showing fragmentation on 501 (M\u003csup\u003e+\u003c/sup\u003e) C\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e, C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 354), C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 261), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eO (m/z 94), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e (m/z 86), C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003e (m/z 78), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e3\u003c/sub\u003eNS (m/z 85), C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eOS (m/z89).\u003csup\u003e13\u003c/sup\u003eC NMR (300 MHz, DMSO-\u003cem\u003ed\u003c/em\u003e\u003csub\u003e6\u003c/sub\u003e) 67.9, 48.2, 54.5, 54.8, 54.4, 54.3, 53.6. 77.2, 77.2, 111.4, 120.5, 126.4, 140.4, 162.4.\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\u003eCharacterization data of compounds 3(a-l).\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"10\"\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 \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c7\" colnum=\"7\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c8\" colnum=\"8\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c9\" colnum=\"9\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c10\" colnum=\"10\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eComp\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eR*\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eMol Formula\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eRF\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eM. P.\u003c/p\u003e \u003cp\u003e(\u0026deg;C)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eYield\u003c/p\u003e \u003cp\u003e(%)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colspan=\"4\" nameend=\"c10\" namest=\"c7\"\u003e \u003cp\u003eAnalysis fond\u003c/p\u003e \u003cp\u003e(calcd)% (obs)\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eValue Eluent\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c7\"\u003e \u003cp\u003eC\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c8\"\u003e \u003cp\u003eH\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c9\"\u003e \u003cp\u003eN\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c10\"\u003e \u003cp\u003eS\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\u003e3a\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-H\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e17\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.81\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e128\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e71\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e62.5\u003c/p\u003e \u003cp\u003e(62.9)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4.2\u003c/p\u003e \u003cp\u003e(4.7)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e8.5\u003c/p\u003e \u003cp\u003e(8.7)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e19.6\u003c/p\u003e \u003cp\u003e(19.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3b\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2-OH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.91\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e137\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e67\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e61.01\u003c/p\u003e \u003cp\u003e(61.74)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e3.95\u003c/p\u003e \u003cp\u003e(3.4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e7.9\u003c/p\u003e \u003cp\u003e(7.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e18.0\u003c/p\u003e \u003cp\u003e(18.1)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3c\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e3-OH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.87\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e131\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e65\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e61.01\u003c/p\u003e \u003cp\u003e(61.74)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e3.95\u003c/p\u003e \u003cp\u003e(3.4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e7.9\u003c/p\u003e \u003cp\u003e(7.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e18.0\u003c/p\u003e \u003cp\u003e(18.1)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3d\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4-OH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.65\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e130\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e58\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e61.01\u003c/p\u003e \u003cp\u003e(61.74)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e3.95\u003c/p\u003e \u003cp\u003e(3.4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e7.9\u003c/p\u003e \u003cp\u003e(7.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e18.0\u003c/p\u003e \u003cp\u003e(18.1)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3e\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2-NO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.41\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e148\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e68\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e56.8\u003c/p\u003e \u003cp\u003e(56.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e3.1\u003c/p\u003e \u003cp\u003e(3.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e11.1\u003c/p\u003e \u003cp\u003e(11.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e16.8\u003c/p\u003e \u003cp\u003e(16.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3f\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e3-NO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.57\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e144\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e64\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e56.8\u003c/p\u003e \u003cp\u003e(56.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e3.1\u003c/p\u003e \u003cp\u003e(3.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e11.1\u003c/p\u003e \u003cp\u003e(11.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e16.8\u003c/p\u003e \u003cp\u003e(16.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3g\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4-NO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.74\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e147\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e81\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e56.8\u003c/p\u003e \u003cp\u003e(56.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e3.1\u003c/p\u003e \u003cp\u003e(3.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e11.1\u003c/p\u003e \u003cp\u003e(11.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e16.8\u003c/p\u003e \u003cp\u003e(16.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3h\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003eCl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.52\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e153\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e66\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e37.3\u003c/p\u003e \u003cp\u003e(37.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4.7\u003c/p\u003e \u003cp\u003e(4.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e11.1\u003c/p\u003e \u003cp\u003e(11.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e25.4\u003c/p\u003e \u003cp\u003e(25.3)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3i\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eON\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003eCl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.65\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e157\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e74\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e37.3\u003c/p\u003e \u003cp\u003e(37.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4.7\u003c/p\u003e \u003cp\u003e(4.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e11.1\u003c/p\u003e \u003cp\u003e(11.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e25.4\u003c/p\u003e \u003cp\u003e(25.3)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3j\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2-OCH3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.93\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e158\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e66\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e58.0\u003c/p\u003e \u003cp\u003e(58.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4.3\u003c/p\u003e \u003cp\u003e(4.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e7.3\u003c/p\u003e \u003cp\u003e(7.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e17.2\u003c/p\u003e \u003cp\u003e(17.8)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3k\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4-OCH3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e167\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e77\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e58.0\u003c/p\u003e \u003cp\u003e(58.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4.3\u003c/p\u003e \u003cp\u003e(4.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e7.3\u003c/p\u003e \u003cp\u003e(7.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e17.2\u003c/p\u003e \u003cp\u003e(17.8)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3l\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e3, 4, 5 (OCH\u003csub\u003e3\u003c/sub\u003e)\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e21\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eO\u003csub\u003e5\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.45\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e177\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e72\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e56.7\u003c/p\u003e \u003cp\u003e(56.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4.5\u003c/p\u003e \u003cp\u003e(4.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e6.5\u003c/p\u003e \u003cp\u003e(6.4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e14.9\u003c/p\u003e \u003cp\u003e(14.6)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003e*Solvent for crystallization: aq. Ethanol for 3a-i; methanol for 3j-l.\u003c/p\u003e \u003cp\u003ea Eluents for TLC: ethyl acetate-acetone (6:4) for 3a, 3b, 3c, 3d, 3f ethyl acetate-acetone (7:3) for 3e, 3g, 3h, 3j, 3k, 3l.\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\u003eCharacterization data of compounds (4a-l).\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"13\"\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=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c7\" colnum=\"7\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c8\" colnum=\"8\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c9\" colnum=\"9\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c10\" colnum=\"10\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c11\" colnum=\"11\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c12\" colnum=\"12\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c13\" colnum=\"13\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eComp\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eR\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eMol Formula\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eRF\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eM. P.\u003c/p\u003e \u003cp\u003e(\u0026deg;C)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eYield\u003c/p\u003e \u003cp\u003e(%)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colspan=\"7\" nameend=\"c13\" namest=\"c7\"\u003e \u003cp\u003eAnalysis found\u003c/p\u003e \u003cp\u003e(calcd)% (obs)\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eValue Eluent\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c7\"\u003e \u003cp\u003eC\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colspan=\"2\" nameend=\"c9\" namest=\"c8\"\u003e \u003cp\u003eH\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colspan=\"2\" nameend=\"c11\" namest=\"c10\"\u003e \u003cp\u003eN\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colspan=\"2\" nameend=\"c13\" namest=\"c12\"\u003e \u003cp\u003eS\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\u003e4a\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-H\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.72\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e172\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e57.14\u003c/p\u003e \u003cp\u003e(57.1)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c9\" namest=\"c8\"\u003e \u003cp\u003e5.2\u003c/p\u003e \u003cp\u003e(5.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c11\" namest=\"c10\"\u003e \u003cp\u003e5.12\u003c/p\u003e \u003cp\u003e(5.7)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c13\" namest=\"c12\"\u003e \u003cp\u003e11.2\u003c/p\u003e \u003cp\u003e(11.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4b\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2-OH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.53\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e177\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e67\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e55.5\u003c/p\u003e \u003cp\u003e(55.7)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c9\" namest=\"c8\"\u003e \u003cp\u003e5.3\u003c/p\u003e \u003cp\u003e(5.0)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c11\" namest=\"c10\"\u003e \u003cp\u003e4.9\u003c/p\u003e \u003cp\u003e(4.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c13\" namest=\"c12\"\u003e \u003cp\u003e11.3\u003c/p\u003e \u003cp\u003e(11.8)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4c\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e3-OH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.45\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e171\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e65\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e55.5\u003c/p\u003e \u003cp\u003e(55.7)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c9\" namest=\"c8\"\u003e \u003cp\u003e5.3\u003c/p\u003e \u003cp\u003e(5.0)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c11\" namest=\"c10\"\u003e \u003cp\u003e4.9\u003c/p\u003e \u003cp\u003e(4.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c13\" namest=\"c12\"\u003e \u003cp\u003e11.3\u003c/p\u003e \u003cp\u003e(11.8)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4d\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4-OH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.92\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e176\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e68\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e55.5\u003c/p\u003e \u003cp\u003e(55.7)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c9\" namest=\"c8\"\u003e \u003cp\u003e5.3\u003c/p\u003e \u003cp\u003e(5.0)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c11\" namest=\"c10\"\u003e \u003cp\u003e4.9\u003c/p\u003e \u003cp\u003e(4.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c13\" namest=\"c12\"\u003e \u003cp\u003e11.3\u003c/p\u003e \u003cp\u003e(11.8)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4e\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2-NO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e29\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.45\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e185\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e58\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e52.7\u003c/p\u003e \u003cp\u003e(52.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c9\" namest=\"c8\"\u003e \u003cp\u003e4.4\u003c/p\u003e \u003cp\u003e(4.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c11\" namest=\"c10\"\u003e \u003cp\u003e7.1\u003c/p\u003e \u003cp\u003e(7.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c13\" namest=\"c12\"\u003e \u003cp\u003e10.7\u003c/p\u003e \u003cp\u003e(10.8)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4f\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e3-NO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e29\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.43\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e159\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e78\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e52.7\u003c/p\u003e \u003cp\u003e(52.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c9\" namest=\"c8\"\u003e \u003cp\u003e4.4\u003c/p\u003e \u003cp\u003e(4.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c11\" namest=\"c10\"\u003e \u003cp\u003e7.1\u003c/p\u003e \u003cp\u003e(7.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c13\" namest=\"c12\"\u003e \u003cp\u003e10.7\u003c/p\u003e \u003cp\u003e(10.8)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4g\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4-NO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e29\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.65\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e182\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e83\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e52.7\u003c/p\u003e \u003cp\u003e(52.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c9\" namest=\"c8\"\u003e \u003cp\u003e4.4\u003c/p\u003e \u003cp\u003e(4.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c11\" namest=\"c10\"\u003e \u003cp\u003e7.1\u003c/p\u003e \u003cp\u003e(7.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c13\" namest=\"c12\"\u003e \u003cp\u003e10.7\u003c/p\u003e \u003cp\u003e(10.8)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4h\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003eCl\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.64\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e173\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e76\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e53.5\u003c/p\u003e \u003cp\u003e(53.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c9\" namest=\"c8\"\u003e \u003cp\u003e5.3\u003c/p\u003e \u003cp\u003e(5.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c11\" namest=\"c10\"\u003e \u003cp\u003e4.8\u003c/p\u003e \u003cp\u003e(4.4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c13\" namest=\"c12\"\u003e \u003cp\u003e11.0\u003c/p\u003e \u003cp\u003e(11.8)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4i\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003eCl\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.55\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e166\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e75\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e53.5\u003c/p\u003e \u003cp\u003e(53.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c9\" namest=\"c8\"\u003e \u003cp\u003e5.0\u003c/p\u003e \u003cp\u003e(5.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c11\" namest=\"c10\"\u003e \u003cp\u003e4.8\u003c/p\u003e \u003cp\u003e(4.4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c13\" namest=\"c12\"\u003e \u003cp\u003e11.0\u003c/p\u003e \u003cp\u003e(11.8)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4j\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2-OCH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e31\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003e S\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.47\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e143\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e67\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e56.5\u003c/p\u003e \u003cp\u003e(56.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e5.3\u003c/p\u003e \u003cp\u003e(5.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c10\" namest=\"c9\"\u003e \u003cp\u003e4.3\u003c/p\u003e \u003cp\u003e(4.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c12\" namest=\"c11\"\u003e \u003cp\u003e11.7\u003c/p\u003e \u003cp\u003e(11.8)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"1\" nameend=\"c13\" namest=\"c13\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4k\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4-OCH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e31\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003e S\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.56\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e173\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e87\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e56.5\u003c/p\u003e \u003cp\u003e(56.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c9\" namest=\"c8\"\u003e \u003cp\u003e5.3\u003c/p\u003e \u003cp\u003e(5.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c11\" namest=\"c10\"\u003e \u003cp\u003e4.3\u003c/p\u003e \u003cp\u003e(4.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c13\" namest=\"c12\"\u003e \u003cp\u003e11.7\u003c/p\u003e \u003cp\u003e(11.8)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4l\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e3, 4, 5 (OCH\u003csub\u003e3\u003c/sub\u003e)\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e29\u003c/sub\u003eH\u003csub\u003e38\u003c/sub\u003eO\u003csub\u003e10\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.86\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e178\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e78\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e54.5\u003c/p\u003e \u003cp\u003e(54.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c9\" namest=\"c8\"\u003e \u003cp\u003e5.9\u003c/p\u003e \u003cp\u003e(5.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c11\" namest=\"c10\"\u003e \u003cp\u003e4.3\u003c/p\u003e \u003cp\u003e(4.4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c13\" namest=\"c12\"\u003e \u003cp\u003e10.7\u003c/p\u003e \u003cp\u003e(10.8)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003e*Solvent for crystallization: aq. Ethanol for 4a-i; methanol for 4j-l.\u003c/p\u003e \u003cp\u003eA Eluents for TLC: ethyl acetate-chloroform(8:2) for 4a, 4b, 4c, 4d, 4f ethyl acetate-acetone (6:4) for 4e, 4g, 4h, 4j, 4k, 4l.\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\u003eCharacterization data of compounds (5a-l).\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"10\"\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=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c7\" colnum=\"7\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c8\" colnum=\"8\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c9\" colnum=\"9\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c10\" colnum=\"10\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eComp\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eR*\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eMol Formula\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eRF\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eM. P.\u003c/p\u003e \u003cp\u003e(\u0026deg;C)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eYield\u003c/p\u003e \u003cp\u003e(%)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colspan=\"4\" nameend=\"c10\" namest=\"c7\"\u003e \u003cp\u003eAnalysis found\u003c/p\u003e \u003cp\u003e(calcd)% (obs)\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eValue Eluent\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c7\"\u003e \u003cp\u003eC\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c8\"\u003e \u003cp\u003eH\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c9\"\u003e \u003cp\u003eN\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c10\"\u003e \u003cp\u003eS\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\u003e5a\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-H\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eCl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.44\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e197\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e77\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e64.77\u003c/p\u003e \u003cp\u003e(64.1)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4.2\u003c/p\u003e \u003cp\u003e(4.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e11.9\u003c/p\u003e \u003cp\u003e(11.7)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e9.7\u003c/p\u003e \u003cp\u003e(9.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5b\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2-OH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eCl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.54\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e187\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e87\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e65.76\u003c/p\u003e \u003cp\u003e(65.74)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4.0\u003c/p\u003e \u003cp\u003e(4.0)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e16.1\u003c/p\u003e \u003cp\u003e(16.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e9.7\u003c/p\u003e \u003cp\u003e(9.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5c\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e3-OH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eCl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.57\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e176\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e65\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e65.76\u003c/p\u003e \u003cp\u003e(65.74)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4.0\u003c/p\u003e \u003cp\u003e(4.0)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e16.1\u003c/p\u003e \u003cp\u003e(16.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e9.7\u003c/p\u003e \u003cp\u003e(9.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5d\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4-OH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eCl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.66\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e176\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e58\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e65.76\u003c/p\u003e \u003cp\u003e(65.74)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4.0\u003c/p\u003e \u003cp\u003e(4.0)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e16.1\u003c/p\u003e \u003cp\u003e(16.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e9.7\u003c/p\u003e \u003cp\u003e(9.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5e\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2-NO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003eN\u003csub\u003e4\u003c/sub\u003eCl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.74\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e181\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e68\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e60.7\u003c/p\u003e \u003cp\u003e(60.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e3.4\u003c/p\u003e \u003cp\u003e(3.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e18.1\u003c/p\u003e \u003cp\u003e(18.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e9.7\u003c/p\u003e \u003cp\u003e(9.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5f\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e3-NO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003eN\u003csub\u003e4\u003c/sub\u003eCl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.73\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e189\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e64\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e60.7\u003c/p\u003e \u003cp\u003e(60.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e3.4\u003c/p\u003e \u003cp\u003e(3.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e18.1\u003c/p\u003e \u003cp\u003e(18.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e9.7\u003c/p\u003e \u003cp\u003e(9.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5g\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4-NO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003eN\u003csub\u003e4\u003c/sub\u003eCl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.44\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e184\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e81\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e67.5\u003c/p\u003e \u003cp\u003e(67.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e5.3\u003c/p\u003e \u003cp\u003e(5.1)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e18.7\u003c/p\u003e \u003cp\u003e(18.5)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e9.7\u003c/p\u003e \u003cp\u003e(9.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5h\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eCl\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.53\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e183\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e66\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e62.5\u003c/p\u003e \u003cp\u003e(62.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e5.3\u003c/p\u003e \u003cp\u003e(5.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e15.3\u003c/p\u003e \u003cp\u003e(15.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e9.7\u003c/p\u003e \u003cp\u003e(9.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5i\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4-Cl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eCl\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.64\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e168\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e77\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e66.5\u003c/p\u003e \u003cp\u003e(66.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4.3\u003c/p\u003e \u003cp\u003e(4.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e15.5\u003c/p\u003e \u003cp\u003e(15.4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e9.7\u003c/p\u003e \u003cp\u003e(9.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5j\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2-OCH3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eCl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.72\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e183\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e66\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e62.5\u003c/p\u003e \u003cp\u003e(62.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e5.3\u003c/p\u003e \u003cp\u003e(5.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e15.3\u003c/p\u003e \u003cp\u003e(15.2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e9.7\u003c/p\u003e \u003cp\u003e(9.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5k\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4-OCH3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eCl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.89\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e187\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e77\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e66.5\u003c/p\u003e \u003cp\u003e(66.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4.3\u003c/p\u003e \u003cp\u003e(4.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e15.5\u003c/p\u003e \u003cp\u003e(15.4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e9.7\u003c/p\u003e \u003cp\u003e(9.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5l\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2-N (CH3)2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC\u003csub\u003e21\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e4\u003c/sub\u003eCl\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.23\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e170\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e77\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e66.5The brominating reagent was combined with 21.6 g of finely \u003c/p\u003e \u003cp\u003e(66.6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4.3\u003c/p\u003e \u003cp\u003e(4.3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e15.5\u003c/p\u003e \u003cp\u003e(15.4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e9.7\u003c/p\u003e \u003cp\u003e(9.4)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003e*Solvent for crystallization: aq. Ethanol for 5a-i; methanol for 5j-l.\u003c/p\u003e \u003cp\u003ea Eluents for TLC: ethyl acetate-acetone (7:3) for 5a, 5b, 5c, 5d, 5f ethyl acetate-acetone (6:4) for 5e, 5g, 5h, 5j, 5k, 5l.\u003c/p\u003e \u003c/div\u003e \u003c/div\u003e"},{"header":"3. Biological activities","content":"\u003cp\u003eComparative study of 4-(2-amino-1, 3-thiazol-4-yl) Phenol (1) and compounds 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one \u003cb\u003e3(a-l)\u003c/b\u003e, 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one \u003cb\u003e4(a-l)\u003c/b\u003e and 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one \u003cb\u003e5(a-l)\u003c/b\u003e have been observed by using Norfloxacine and Griseofulvin as standards. The enhancement in biological activity of compound \u003cb\u003e(1)\u003c/b\u003e as compared with the newly synthesized \u003cb\u003e3(a-i)\u003c/b\u003e, \u003cb\u003e4(a-l)\u003c/b\u003e, \u003cb\u003e5(a-l)\u003c/b\u003e has been observed. The synthesized compounds were tested at 100 ug/ml concentrations against \u003cem\u003eEscherichia coli\u003c/em\u003e, Pseudomonas \u003cem\u003eaeruginosa\u003c/em\u003e, \u003cem\u003eStaphylococcus aureus\u003c/em\u003e, \u003cem\u003eProteus vulgaris\u003c/em\u003e and fungal cultures such as \u003cem\u003eAspergillus niger\u003c/em\u003e and \u003cem\u003eCandida albicans\u003c/em\u003e for its antibacterial and antifungal screening as shown in Tables\u0026nbsp;\u003cspan refid=\"Tab4\" class=\"InternalRef\"\u003e4\u003c/span\u003e, \u003cspan refid=\"Tab5\" class=\"InternalRef\"\u003e5\u003c/span\u003e, and \u003cspan refid=\"Tab6\" class=\"InternalRef\"\u003e6\u003c/span\u003e.\u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab4\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 4\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eData for in vitro antibacterial and anti-fungal activities (in mm)\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"7\"\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=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c7\" colnum=\"7\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eComp.\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colspan=\"6\" nameend=\"c7\" namest=\"c2\"\u003e \u003cp\u003eMinimum inhibitory concentration\u0026rsquo;s g/ml\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eE. \u003cem\u003eColi\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eS. \u003cem\u003eaurous\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003ePs. \u003cem\u003eaeruginosa\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eP. \u003cem\u003eVulgaris\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\"\u003e \u003cp\u003eA. \u003cem\u003eniger\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c7\"\u003e \u003cp\u003eC. \u003cem\u003ealbicans\u003c/em\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\u003e3a\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e20\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3b\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e16\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e24\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3c\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e18\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e16\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3d\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3e\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e20\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e22\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3f\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e21\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3g\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3h\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eNA\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3i\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eNA\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e18\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3j\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003eNA\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3k\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3l\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e18\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e16\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003eNA: not active; -: no inhibition of growth.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab5\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 5\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eData for in vitro antibacterial and anti-fungal activities (in mm)\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"7\"\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=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c7\" colnum=\"7\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eComp.\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colspan=\"6\" nameend=\"c7\" namest=\"c2\"\u003e \u003cp\u003eMinimum inhibitory concentration\u0026rsquo;s g/ml\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eE. \u003cem\u003eColi\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eS. \u003cem\u003eaurous\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003ePs. \u003cem\u003eaeruginosa\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eP. \u003cem\u003eVulgaris\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\"\u003e \u003cp\u003eA. \u003cem\u003eniger\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c7\"\u003e \u003cp\u003eC. \u003cem\u003ealbicans\u003c/em\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\u003e4a\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e20\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e19\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4b\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e20\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4c\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4d\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e20\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4e\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e22\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4f\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e21\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4g\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eNA\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4h\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4i\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e18\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e20\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4j\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e16\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4k\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e22\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4l\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eNA\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e18\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003eNA: not active; -: no inhibition of growth.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eTable\u0026nbsp;\u003cspan refid=\"Tab5\" class=\"InternalRef\"\u003e5\u003c/span\u003e \u003cb\u003eData for in vitro antibacterial and anti-fungal activities (in mm).\u003c/b\u003e\u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"No\" id=\"Taba\" border=\"1\"\u003e \u003ccolgroup cols=\"7\"\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=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c7\" colnum=\"7\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eComp.\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colspan=\"6\" nameend=\"c7\" namest=\"c2\"\u003e \u003cp\u003eMinimum inhibitory concentration\u0026rsquo;s g/ml\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eE. \u003cem\u003eColi\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eS. \u003cem\u003eaurous\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003ePs. \u003cem\u003eaeruginosa\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eP. \u003cem\u003eVulgaris\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\"\u003e \u003cp\u003eA. \u003cem\u003eniger\u003c/em\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c7\"\u003e \u003cp\u003eC. \u003cem\u003ealbicans\u003c/em\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\u003e5a\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e20\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e25\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e30\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e35\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5b\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e24\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e30\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5c\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e19\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e20\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5d\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e18\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5e\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e22\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5f\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e20\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e21\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5g\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5h\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5i\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eNA\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e18\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e17\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5j\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e18\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5k\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5l\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eNA\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e18\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003eNA: not active; -: no inhibition of growth.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e"},{"header":"4. Antioxidant activity","content":"\u003cp\u003eThe proportion of free radical scavenging activity revealed by the test compounds 3a-l, 4a-l and 5a-l was quantified using the 1, 1-diphenyl picryl hydrazyl (DPPH) assay technique. Drug stock solutions with concentrations of 1 mg mL-1 in methanol were diluted to produce final concentrations of 2, 4, 6, 8, and 10 mg mL-1. The findings were read after adding a DPPH methanol solution (1 mL, 0.3 M mol) to 2.5 mL of drug solutions with different concentrations and letting the mixture react at room temperature. The proportion of antioxidant activity was determined from the observations made after 30 minutes of observation by measuring the absorbance values at 518 nm. Methanol was applied as the solvent, while ascorbic acid was used as the reference. The estimated percentage of inhibition based on concentration is shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig4\" class=\"InternalRef\"\u003e4\u003c/span\u003e. The outcomes are shown in Table\u0026nbsp;\u003cspan refid=\"Tab6\" class=\"InternalRef\"\u003e6\u003c/span\u003e. Ascorbic acid was the usual medication.\u003c/p\u003e "},{"header":"5. Result and discursion","content":"\u003cp\u003eConsidering the pharmacological properties of thaizolidine, thourea, and 4-hydroxyacetophenone in ethanol as previously described, 4-(2-amino-1, 3-thiazol-4-yl) is formed as the starting material. After combining various aldehydes and stirring for six hours, phenol (1) was transformed into 4-(2-schiffs base-1, 3-thiazol-4-yl) phenol (2) was then undergo cyclisation in presence of glacial acetic acid gives 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one \u003cb\u003e3 (a-l)\u003c/b\u003e and a-D-2, 3, 4, 6-tetra-\u003cem\u003eO\u003c/em\u003e-acetyl Glucopyranosyl bromide were dissolved in dioxane at 100\u003csup\u003e0\u003c/sup\u003eC and kept at this temperature for 4 hours to give 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one \u003cb\u003e4 (a-l)\u003c/b\u003e and 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one \u003cb\u003e5 (a-l)\u003c/b\u003e. Among the series of compounds created, compounds 3(a-l), 4(a-l), and 5(a-l) with (hydroxyl phenyl, nitro phenyl, chlorophenyl, methoxyphenyl, and N (di-methylphenyl) have demonstrated good antioxidant activity. In order to find a possible pharmacophore, these chemicals will therefore be further investigated for their antibacterial properties.\u003c/p\u003e"},{"header":"6. Conclusion","content":"\u003cp\u003eThe findings of this investigation show that the current O-(β -D-Glucopyranosyl) synthetic approach is a straightforward, effective, affordable, and simple way to synthesize molecules with biological activity 3-[4-(phenyl-4-hydroxy)3-thiazole-2-yl] --2-phenyl-1, 3-thiazolidin-4-one 3(a-l), 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one \u003cb\u003e4(a-l)\u003c/b\u003e and 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one \u003cb\u003e5(a-l)\u003c/b\u003e. Compared to basic Thaizolidine, these compounds demonstrated good performance at concentrations of 100 ug/ml against a variety of bacteria and viruses, including Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Proteus vulgaris, and fungal cultures including Aspergillus niger and Candida albicans. The compounds 3-[4-(4-hydroxy phenyl)-1, 3-thiazole-2-yl]-2-phenyl-1, 3-thiazolidin-4-one \u003cb\u003e3(a-l)\u003c/b\u003e, 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one \u003cb\u003e4(a-l)\u003c/b\u003e and 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one \u003cb\u003e5(a-l)\u003c/b\u003e have shown good antioxidant activity.\u003c/p\u003e"},{"header":"Declarations","content":"\u003ch2\u003eDeclaration of competing interest\u003c/h2\u003e \u003cp\u003eThe authors affirm that they have no financial stake in the outcome of the work described in the publication.\u003c/p\u003e\u003ch2\u003eSupplementary data\u003c/h2\u003e \u003cp\u003eSupplementary data to this manuscript can be found online.\u003c/p\u003e\u003cp\u003e\u003cstrong\u003eCompeting Interests\u003c/strong\u003e\u003cp\u003eThe findings of this investigation show that the current O-(β -D-Glucopyranosyl) synthetic approach is a straightforward, effective, affordable, and simple way to synthesize molecules with biological activity 3-[4-(phenyl-4-hydroxy)3-thiazole-2-yl] --2-phenyl-1, 3-thiazolidin-4-one 3(a-l), 3-[4-(4- O-(2, 3, 4, 6- tetra- O- acetyl- β- D- Glucopyranosyl)phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 4(a-l) and 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one 5(a-l). Compared to basic Thaizolidine, these compounds demonstrated good performance at concentrations of 100 ug/ml against a variety of bacteria and viruses, including Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Proteus vulgaris, and fungal cultures including Aspergillus niger and Candida albicans.\u003c/p\u003e\u003c/p\u003e\u003ch2\u003eAuthor Contribution\u003c/h2\u003e\u003cp\u003eThere is no any conflict of inference in Synthesis of 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one, Chanda W. Awaghade1prepared figures 1-3, Meghasham N. Narule*wrote the main manuscript text , Niren Kathale1, 1Department of Chemistry, Sardar Patel Mahavidyalaya, Chandrapur. Department of Chemistry, Vidya Vikas Arts, Commerce \u0026amp; Science College, Samudrapur, Dist-Wardha, 442305, INDIA. All authors reviewed the manuscript\u003c/p\u003e\u003ch2\u003eAcknowledgement\u003c/h2\u003e \u003cp\u003eThe Director SAIF Punjab University Chandigarh is thanked by the author for supplying spectral and analytical data.\u003c/p\u003e\u003ch2\u003eData availability\u003c/h2\u003e \u003cp\u003eData will be made available on request.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\u003cli\u003e\u003cspan\u003eOstrovskii, V.A.; Koldobskii, G.I.; Trifonov, R.E. Tetrazoles. In Comprehensive Heterocyclic Chemistry III;Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., Taylor, R.J.K., Eds.; Elsevier: Oxford, UK, 2008; Volume 6,pp. 257\u0026ndash;423.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eCouri, M.R.; Luduvico, I.; Santos, L.; Alves, R.; Prado, M.A.; Gil, R.F. Microwave-assisted efficient preparation of novel carbohydrate tetrazole derivatives. Carbohydr. 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Narule, \u0026ldquo;Synthesis of 2-Aryl-3-[4/-Phenyl Thiazolidinyl]-4-Oxo- Thiazolidines\u0026rdquo; Journal of Gujarat Chemical Society, 2020, 0374\u0026ndash;8588.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eM Narule, J Meshram, Microwave mediated synthesis of biologically active 2-(4'-phenothiazinyl pyrazolyl) pyrroles, Indian Journal of Heterocyclic Chemistry, 2006, 16 (2), 189\u0026ndash;190.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eM N Narule, JS Meshram, Advanced polymers for high technology applications, CSIR, 2006.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eM Narule, J Meshram, Environmental acceptable synthesis of 2-[(5/-(substituted phenyl)-1/-phenyl) pyrazolyl] pyrroles, Current World Environment, 2006, 1 (1), 45.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eJ Meshram, A Kathale, MN Narule, Synthesis and Characterization of new 2-furyl-3-aryl-4-thiazolidinones, Oriental Journal of Chemistry, 2006, 22 (2), 285.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eQuale J, Landman D, Ravishankar J, Flores C, Bratu S. Streptococcus pneumoniae, Brooklyn, New York: fluoroqu- inolone resistance at our doorstep. Emerg Infect Dis 2002; 8: 594\u0026ndash;597.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eHo PL. Decreased levofloxacin susceptibility in Haemo-philus influenzae in children, Hong Kong. Emerg Infect Dis 2004; 10: 1960\u0026ndash;1962.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eCalvo J, Martinez L. Mecanismos de acci\u0026oacute;nn de los antimicrobianos. Enferm Infecc Microbiol Clin., 2009; 27(1): 44\u0026ndash;52.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eAldred KJ, Kerns RJ, Osheroff N. Mechanism of Quinolone Action and Resistance. Biochemistry, 2014; 53: 1565\u0026ndash;1574.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003ePallares R, Fenoll A, Linares J. The epidemiology of antibiotic resistance in Streptococcus pneumoniae and the clinical relevance of resistance to cephalosporins, macro- lides and quinolones. Int J Antimicrob Agents 2003; 22(suppl 1): S15\u0026ndash;S24.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eFriedland I, Gallagher G, King T, Woods GL. Antimi- crobial susceptibility patterns in Pseudomonas aeruginosa: data from a multicenter Intensive Care Unit Surveillance Study (ISS) in the United States. J Chemother 2004; 16: 437\u0026ndash;441.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eBlandino G, Marchese A, Ardito F et al. Antimicrobial susceptibility profiles of Pseudomonas aeruginosa and Staphylococcus aureus isolated in Italy from patients withhospital-acquired infections. Int J Antimicrob Agents 2004; 24: 515\u0026ndash;518.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eAhmed A, Daneshtalab M. Nonclassical biological activities of quinolone derivatives. J Pharm Pharmaceut Sci., 2012; 15(1): 52\u0026ndash;72.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eEmmerson AM, Jones A M. The quinolones: decades of development and use J. Antimicrob. Chemotherapy, 2003; 51: 13\u0026ndash;20.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eSprandel KA, Rodvold KA. Safety and tolerability of fluoroquinolones. Clin Cornerstone Suppl 2003; 3: S29\u0026ndash;S36.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eAndersson MI, MacGowan AP. Development of the quinolones. J Antimicrob hemother 2003; 51(suppl 1): 1\u0026ndash;11.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eBoteva AA, Krasnykh OP. The methods os synthesis, modification and biological activity of 4-quinolones (Review). Chem. of Heter. Compounds, 2009; 45(7): 757\u0026ndash;785.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eCunha BA. Empiric therapy of community-acquired pneumonia: guidelines for the perplexed? Chest 2004; 125: 1913\u0026ndash;1919.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eBlondeau JM, Missaghi B. 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The Journal of Organic Chemistry 2019, \u003cem\u003e84\u003c/em\u003e (11), 6946\u0026ndash;6961.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eLeleti Rajender Reddy, Yogesh Waman, Krishna Nayak, Kasimraza Baharooni, Sharadsrikar Kotturi. Asymmetric Synthesis 1-Substituted 2, 6-Diazaspiro[3.3]heptanes through Addition of 3-Azetidinecarboxylate Anions to Davis\u0026ndash;Ellman Imines. Organic Letters 2019, \u003cem\u003e21\u003c/em\u003e (10), 3481\u0026ndash;3484.\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eAlexander J. Boddy, Christopher J. Cordier, Kristin Goldberg, Andrew Madin, Alan C. Spivey, James A. Bull. Acid-Mediated Ring Expansion of 2,2-Disubstituted Azetidine Carbamates to 6,6-Disubstituted 1,3-Oxazinan-2-ones. Organic Letters 2019, \u003cem\u003e21\u003c/em\u003e (6), 1818\u0026ndash;1822.\u003c/span\u003e\u003c/li\u003e\u003c/ol\u003e"},{"header":"Table 6","content":"\u003cp\u003eTable 6 is available in the Supplementary Files section.\u003c/p\u003e"},{"header":"scheme 1","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":true,"highlight":"","institution":"","isAcceptedByJournal":false,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true},"keywords":"Heterocyclic, O-(β -D-Glucopyranosyl) derivatives, Thizole, Thaizolidine, Biological activities, etc","lastPublishedDoi":"10.21203/rs.3.rs-5317015/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-5317015/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eThe current study's objective was to create a novel antibacterial agent. Numerous unique heterocyclic O-(β-D-Glucopyranosyl) derivatives have been developed for investigation based on their pharmacological properties in the search for new medications. Synthesis of 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl] -2-phenyl-1, 3-thiazolidin-4-one, which were produced through additions between various acetophenone and urea in a glycosylation. In comparison to standard drugs Norfloxacine and Griseofulvin, these compounds exhibit antibacterial and antifungal activities against bacterial cultures, including Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Proteus vulgaris, and fungal cultures, include Aspergillus Niger and Candida albicans. IR, 1HNMR, and elemental analysis have all verified the compounds' structures. In order to achieve possible pharmacophoric action, these compounds will therefore undergo additional testing.\u003c/p\u003e","manuscriptTitle":"Synthesis of novel 3-[4-(4- O-(β -D-Glucopyranosyl) phenyl)-1, 3-thiazol-2-yl]-2-phenyl-1, 3-thiazolidin-4-one as antioxidant agent","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2024-11-05 08:52:50","doi":"10.21203/rs.3.rs-5317015/v1","editorialEvents":[{"type":"communityComments","content":0}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"830b28d1-0b30-408d-a54d-90477e264728","owner":[],"postedDate":"November 5th, 2024","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"posted","subjectAreas":[],"tags":[],"updatedAt":"2024-11-12T07:08:59+00:00","versionOfRecord":[],"versionCreatedAt":"2024-11-05 08:52:50","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-5317015","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-5317015","identity":"rs-5317015","version":["v1"]},"buildId":"qtupq5eGEP_6zYnWcrvyt","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}