Theoretical, X-Ray Structural and Spectroscopic Analysis of a Novel Synthetic Conversion of Isatin to Tryptanthrin

Theoretical, X-Ray Structural and Spectroscopic Analysis of a Novel Synthetic Conversion of Isatin to Tryptanthrin | 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 Theoretical, X-Ray Structural and Spectroscopic Analysis of a Novel Synthetic Conversion of Isatin to Tryptanthrin Niyazi Demirci, Seda Günesdogdu Sagdınç, Salih Zeki Yildiz This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-9658170/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 Tryptanthrin (indolo[2,1-b] quinazoline-6,12-dione) (TRYP) exhibits various biological activities as hydrocarbon receptor agonist, anticancer and antitrypanosomal activities. The synthetic conversion of isatin to tryptanthrin has been investigated for a long time, and in this study, Tryptanthrin was synthesized from isatin through a novel, carbohydrazide-mediated route. The reaction conditions were optimized using DMF as a solvent under reflux, providing a new alternative to traditional oxidative methods. The structure of the synthesized tryptanthrin has been determined using X-ray single crystallography, spectroscopic techniques (UV-Vis and FT-IR), and theoretical calculations have been performed to support the proposed structure. The close intermolecular interactions of the tryptanthrin have been investigated using Hirshfeld surface and fingerprint plot analyses. The geometrical structural parameters, atomic charges, natural bond orbitals (NBOs), natural hybrid orbitals (NHOs), vibrational frequencies and nonlinear optical properties (NLOs) of tryptanthrin have been investigated using DFT/B3LYP/6-311 + + G(2df, 2pd) method. The electronic properties and the transitions for UV-Vis spectrum analysis have been calculated by using TD-DFT/B3LYP/6-311 + + G(2df, 2pd) method. The detailed IR assignments have been performed using the potential energy distribution (PED) analysis with VEDA4 program. The recorded experimental spectra (UV-Vis and FT-IR) of tryptanthrin are in good agreement with their theoretical spectra. Tryptanthrin synthesis Hirshfeld surface analysis DFT UV-Vis FT-IR Full Text Additional Declarations No competing interests reported. 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. 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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-9658170","acceptedTermsAndConditions":true,"allowDirectSubmit":true,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":637123402,"identity":"ebeba34d-a153-4d50-a19c-b0d0b3e75ee5","order_by":0,"name":"Niyazi Demirci","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAA20lEQVRIiWNgGAWjYFCCBDDiYWNvPvgAyOXhI1oLH8+xZAOQFjaitICAnESOmQSIQVCLOXvy0Q0P99jJsDGkpVV+zQExmB8+uoFHi2XPs7QbCc+Sge45fOy27DYQg83YOAePFoMbOWY3Eg4c4GFjbEu7LbmNGaiFh00av5b8bxAtzDxmxZLb6onRksMG0cLGY8b4cdthIrSceQZyGNALPGzJ0ozbjgOtI+SX48nPbv44YGcvP//xwY8/t1Xb87M3P3yMTwsKYOYBk8QqBwHGH6SoHgWjYBSMghEDABSZRz+a0pQkAAAAAElFTkSuQmCC","orcid":"","institution":"Kocaeli University","correspondingAuthor":true,"prefix":"","firstName":"Niyazi","middleName":"","lastName":"Demirci","suffix":""},{"id":637123404,"identity":"eb09871f-4e56-4332-b3e5-f03e80a5a782","order_by":1,"name":"Seda Günesdogdu Sagdınç","email":"","orcid":"","institution":"Kocaeli University","correspondingAuthor":false,"prefix":"","firstName":"Seda","middleName":"Günesdogdu","lastName":"Sagdınç","suffix":""},{"id":637123406,"identity":"24553cfa-39d6-4e93-a0a8-6bb0aaa02e06","order_by":2,"name":"Salih Zeki Yildiz","email":"","orcid":"","institution":"Sakarya University","correspondingAuthor":false,"prefix":"","firstName":"Salih","middleName":"Zeki","lastName":"Yildiz","suffix":""}],"badges":[],"createdAt":"2026-05-08 22:08:17","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-9658170/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-9658170/v1","draftVersion":[],"editorialEvents":[],"editorialNote":"","failedWorkflow":false,"files":[{"id":109068174,"identity":"8eb4e7eb-4e49-4820-8ebc-f62b96fdb186","added_by":"auto","created_at":"2026-05-12 10:04:17","extension":"pdf","order_by":1,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":890435,"visible":true,"origin":"","legend":"","description":"","filename":"DemirciTryptanthrinManuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-9658170/v1_covered_d509ccfa-2d49-446f-8eea-eac3ad77a1f4.pdf"}],"financialInterests":"No competing interests reported.","formattedTitle":"Theoretical, X-Ray Structural and Spectroscopic Analysis of a Novel Synthetic Conversion of Isatin to Tryptanthrin","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":"Tryptanthrin, synthesis, Hirshfeld surface analysis, DFT, UV-Vis, FT-IR","lastPublishedDoi":"10.21203/rs.3.rs-9658170/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-9658170/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eTryptanthrin (indolo[2,1-b] quinazoline-6,12-dione) (TRYP) exhibits various biological activities as hydrocarbon receptor agonist, anticancer and antitrypanosomal activities. 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The geometrical structural parameters, atomic charges, natural bond orbitals (NBOs), natural hybrid orbitals (NHOs), vibrational frequencies and nonlinear optical properties (NLOs) of tryptanthrin have been investigated using DFT/B3LYP/6-311\u0026thinsp;+\u0026thinsp;+\u0026thinsp;G(2df, 2pd) method. The electronic properties and the transitions for UV-Vis spectrum analysis have been calculated by using TD-DFT/B3LYP/6-311\u0026thinsp;+\u0026thinsp;+\u0026thinsp;G(2df, 2pd) method. The detailed IR assignments have been performed using the potential energy distribution (PED) analysis with VEDA4 program. 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