Nitrophenyl-Group-Containing Heterocycles. 2. Synthesis, Characterization, Anticancer Activity, Apoptotic Induction and Cell Cycle Arrest of Some New 5,6,7,8-Tetrahydro-isoquinolines Bearing  2-Nitrophenyl  Group

Nitrophenyl-Group-Containing Heterocycles. 2. Synthesis, Characterization, Anticancer Activity, Apoptotic Induction and Cell Cycle Arrest of Some New 5,6,7,8-Tetrahydro-isoquinolines Bearing 2-Nitrophenyl Group | 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 Nitrophenyl-Group-Containing Heterocycles. 2. Synthesis, Characterization, Anticancer Activity, Apoptotic Induction and Cell Cycle Arrest of Some New 5,6,7,8-Tetrahydro-isoquinolines Bearing 2-Nitrophenyl Group Abdelreheem A. Saddik, Etify A. Bakhite, Reda Hassanien, Nasser Farhan, and 2 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-4493252/v2 This work is licensed under a CC BY 4.0 License Status: Posted Version 2 posted You are reading this latest preprint version Show more versions Abstract In this work 7-Acetyl-4-cyano-1, 6-dimethyl-6-hydroxy-8-(2-nitrophenyl)-5,6,7,8-tetrahydrosoquinoline-3(2 H )-thione compound 2 was synthesized and used as starting materials. Subsequently, Compounds 3–7 were produced through its reaction with ethyl iodide, ethyl chloroacetate, chloroacetonitrile, and chloroacetaldehyde. Additionally, compound 2 and 2-chloroacetamide were heated in ethanol with sodium acetate trihydrate present, resulting in the formation of 3-Substituted methylthio-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles 9a–d , respectively. Similarly, compounds 2 and N-(1-naphthyl)-2-chloroacetamide reacted to produce high yields of the equivalent N-(1-naphthyl)-(5,6,7,8-tetrahydroiso-quinolin-3-ylthio)acetamides 9e . Compounds 9a–e were cyclized into their 10a and d. Using elemental analysis and spectral data (FT-IR, 1 H NMR, and 13 C NMR). All newly synthesized compounds were described. The anticancer activity of the produced compounds was also assessed against eight cell lines at one spot concentration and one normal human skin fibroblast cell line HSF . Then determine the IC 50 of our drugs against two specific cell lines using various doses. Compound 3 is the most effective chemical against HEGP2 , according to our research. Compound 9c was also the most effective compound against HCT116 . For generally, the tested substances showed moderate anticancer activity, according to the data. The effects of compound 3 on the proliferation of HEGP2 cell lines were then investigated using an apoptotic Annexin V-FITC assay and flow cytometry. Compound 3 increased the HEGP2 cell line's apoptosis by 50 times and caused cell cycle arrest at the G2/M phase. Biological sciences/Biochemistry Biological sciences/Chemical biology Physical sciences/Chemistry Anticancer Apoptosis cell cycle Synthesis Characterization tetrahydrosoquinoline Full Text Supplementary Files SupplementryInformation.docx Cite Share Download PDF Status: Posted Version 2 posted You are reading this latest preprint version Show more versions 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-4493252","acceptedTermsAndConditions":true,"allowDirectSubmit":true,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":342669444,"identity":"d8ce0555-5eef-11ef-91e4-06cc9d20a69f","order_by":0,"name":"Abdelreheem A. Saddik","email":"","orcid":"","institution":"Assiut University","correspondingAuthor":false,"prefix":"","firstName":"Abdelreheem","middleName":"A.","lastName":"Saddik","suffix":""},{"id":342669631,"identity":"e126bd5d-5eef-11ef-91e4-06cc9d20a69f","order_by":1,"name":"Etify A. 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Synthesis, Characterization, Anticancer Activity, Apoptotic Induction and Cell Cycle Arrest of Some New 5,6,7,8-Tetrahydro-isoquinolines Bearing 2-Nitrophenyl Group","fulltext":[],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":false,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":true,"hideJournal":true,"highlight":"","institution":"","isAcceptedByJournal":false,"isAuthorSuppliedPdf":true,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":true,"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":"Anticancer, Apoptosis, cell cycle, Synthesis, Characterization, tetrahydrosoquinoline","lastPublishedDoi":"10.21203/rs.3.rs-4493252/v2","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-4493252/v2","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eIn this work 7-Acetyl-4-cyano-1, 6-dimethyl-6-hydroxy-8-(2-nitrophenyl)-5,6,7,8-tetrahydrosoquinoline-3(2\u003cem\u003eH\u003c/em\u003e)-thione compound \u003cb\u003e2\u003c/b\u003e was synthesized and used as starting materials. Subsequently, Compounds \u003cb\u003e3\u0026ndash;7\u003c/b\u003e were produced through its reaction with ethyl iodide, ethyl chloroacetate, chloroacetonitrile, and chloroacetaldehyde. Additionally, compound \u003cb\u003e2\u003c/b\u003e and 2-chloroacetamide were heated in ethanol with sodium acetate trihydrate present, resulting in the formation of 3-Substituted methylthio-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles \u003cb\u003e9a\u0026ndash;d\u003c/b\u003e, respectively. Similarly, compounds \u003cb\u003e2\u003c/b\u003e and N-(1-naphthyl)-2-chloroacetamide reacted to produce high yields of the equivalent N-(1-naphthyl)-(5,6,7,8-tetrahydroiso-quinolin-3-ylthio)acetamides \u003cb\u003e9e\u003c/b\u003e. Compounds \u003cb\u003e9a\u0026ndash;e\u003c/b\u003e were cyclized into their \u003cb\u003e10a\u003c/b\u003e and \u003cb\u003ed.\u003c/b\u003e Using elemental analysis and spectral data (FT-IR, \u003csup\u003e1\u003c/sup\u003eH NMR, and \u003csup\u003e13\u003c/sup\u003eC NMR). All newly synthesized compounds were described. The anticancer activity of the produced compounds was also assessed against eight cell lines at one spot concentration and one normal human skin fibroblast cell line \u003cb\u003eHSF\u003c/b\u003e. Then determine the IC\u003csub\u003e50\u003c/sub\u003e of our drugs against two specific cell lines using various doses. Compound \u003cb\u003e3\u003c/b\u003e is the most effective chemical against \u003cb\u003eHEGP2\u003c/b\u003e, according to our research. Compound \u003cb\u003e9c\u003c/b\u003e was also the most effective compound against \u003cb\u003eHCT116\u003c/b\u003e. For generally, the tested substances showed moderate anticancer activity, according to the data. The effects of compound \u003cb\u003e3\u003c/b\u003e on the proliferation of HEGP2 cell lines were then investigated using an apoptotic Annexin V-FITC assay and flow cytometry. 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