A Synthesis of Novel Tetracyclic Azocino[4,3-b]Indole Framework: Combined Spectroscopic, DFT, Molecular Docking, and ADMET Analysis

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dc.contributor.authorUludag, Nesimi
dc.contributor.authorSerin, Sumeyya
dc.contributor.authorUstun, Elvan
dc.contributor.authorSerdaroglu, Goncagul
dc.date.accessioned2026-04-04T13:37:41Z
dc.date.available2026-04-04T13:37:41Z
dc.date.issued2026
dc.departmentİnönü Üniversitesi
dc.description.abstractThe paper describes a new synthetic method for the 1,5-methanoazocino [4,3-b]indole. Starting from 2,3,4,9-tetrahydrospiro[1H-carbazole-1,2'-[1,3]dithiolan]-4(9H)-one I with (1,3-dithiolan-2-yl)methanamine, reduction of imine II with NaBH4 yielded to the amine and benzoylation, N-((1,3-dithiolan-2-yl)methyl)-N-(2,3,4,9-tetrahydrospiro[carbazole-1,2'-[1,3]dithiolan]-4-yl)benzamide III. Compounds IV and V were completed through several steps from III. The resulting structure V underwent an intramolecular aldol reaction using NaH as a base for the cyclization of 2-benzoyle-4-hydroxy-1,2,3,4,5,7-hexehydro-1,5-methanoazocino[4,3-b]indole-6-one VI, which represents the tetracyclic skeleton of Strychnos alkaloids. Besides, quantum chemical computations were conducted on compounds I-VI. Regarding structural parameters and spectroscopic characterization, the experimental and computational data were found to be in good agreement. Also, ADMET, bioavailability, and drug-likeness properties of the data set were determined to provide comprehensive information on structure-activity relationships. The interactions of I-VI against DNA gyrase of E. coli, CYP51 from Candida glabrata, and leukemia inhibitory factor were evaluated with molecular docking for foresight into the possible bioactivities. This comprehensive work hopefully to provide the structural, physical, and chemical properties, which would be important to optimizing the related properties of the molecular systems for biomedical purposes.
dc.description.sponsorshipScientific and Technological Research Council of Turkey [112T503]
dc.description.sponsorshipThis research was financially supported by the Scientific and Technological Research Council of Turkey (TUBITAK Project No. 112T503). The authors also acknowledge Nam & imath;k Kemal University for analyzing the structure of our article. All computations were performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure).
dc.identifier.doi10.1002/cbdv.202503759
dc.identifier.issn1612-1872
dc.identifier.issn1612-1880
dc.identifier.issue2
dc.identifier.pmid41698027
dc.identifier.scopus2-s2.0-105030250044
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1002/cbdv.202503759
dc.identifier.urihttps://hdl.handle.net/11616/109993
dc.identifier.volume23
dc.identifier.wosWOS:001705229000020
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherWiley-V C H Verlag Gmbh
dc.relation.ispartofChemistry & Biodiversity
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WOS_20250329
dc.subjectADMET
dc.subjectDFT studies
dc.subjectmolecular dockings
dc.subjectStrychnos alkaloids
dc.subjecttetracyclic azocino[4,3-b]indole
dc.titleA Synthesis of Novel Tetracyclic Azocino[4,3-b]Indole Framework: Combined Spectroscopic, DFT, Molecular Docking, and ADMET Analysis
dc.typeArticle

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