Single-step approach for synthesis of a novel tetracyclic skeleton: Investigation of X-ray analysis, fluorescence spectra, TD-DFT calculations and biological activities

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dc.authoridBurak Kuzu: 0000-0002-7305-7177en_US
dc.authoridMeltem Tan Uygun: 0000-0003-4190-6047en_US
dc.authoridMesude Figen Dönmez: 0000-0002-7992-8252en_US
dc.authoridNurettin Mengeş: 0000-0002-5990-6275en_US
dc.contributor.authorKuzu, Burak
dc.contributor.authorGül, Sergen
dc.contributor.authorTan Uygun, Meltem
dc.contributor.authorDönmez, Mesude Figen
dc.contributor.authorMengeş, Nurettin
dc.date.accessioned2023-04-07T11:28:20Z
dc.date.available2023-04-07T11:28:20Z
dc.date.issued2023en_US
dc.departmentNEÜ, Mühendislik-Mimarlık Fakültesi, Biyomedikal Mühendisliği Bölümüen_US
dc.descriptionMakaleen_US
dc.descriptionWOS:000904967000006en_US
dc.description.abstractTetracyclic molecules show important properties such as biological activities and fluorescence sensors. Hence, in this study, we have reported unknown tetracyclic skeleton. N -propargylated C-2 and C-4 disubstituted imidazole derivatives were reacted by 2-aminomethyl piperidine without using any transition metal. The reaction unveiled 16 different imidazo[1,2-a]pyrido[1 ' ,2 ' :3,4]imidazo[2,1-c]pyrazine skeletons. Cyclization reaction tolerated phenyl, naphthyl, bi-phenyl, 2-thienyl, and many substituents on the benzene ring such as OMe, CF 3 , and halogens. We have uncovered the exact structure of the tetracyclic skeleton using single-crystal X-ray analysis. Significant fluorescence emission of tetracyclic molecules was investigated, and derivatives bearing electron-withdrawing groups, CF 3 , and the 2-thienyl group possessed a bathochromic effect (shift to longer wavelength) which was confirmed by not only steady-state experiments but HOMOs and LUMOs calculations. The antimicrobial effects of the synthesized molecules on six different or ganisms were tested. Considerable activities of molecules 5p and 5n on many organisms were determined. Docking modeling and Lipinski, Ghose, and Veber compatibility studies of two different molecules were performed.en_US
dc.description.sponsorshipScientific and Technological Research Council of Türkiye (TUBITAK)en_US
dc.identifier.citationKuzu, B., :Gül, S., Tan Uygun, M., Dönmez, M. F., Mengeş, N. (2023). Single-step approach for synthesis of a novel tetracyclic skeleton: Investigation of X-ray analysis, fluorescence spectra, TD-DFT calculations and biological activities. Journal of Molecular Structure, 1273, 1-12.en_US
dc.identifier.doi10.1016/j.molstruc.2022.134311en_US
dc.identifier.endpage12en_US
dc.identifier.issn0022-2860en_US
dc.identifier.issn1872-8014en_US
dc.identifier.issue-en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage1en_US
dc.identifier.urihttp://dx.doi.org/10.1016/j.molstruc.2022.134311
dc.identifier.urihttps://hdl.handle.net/20.500.12452/9393
dc.identifier.volume1273en_US
dc.identifier.wosWOS:000904967000006en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.relation.ispartofJournal of Molecular Structureen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/embargoedAccessen_US
dc.subjectN-propargylated Heterocycleen_US
dc.subjectImidazoleen_US
dc.subjectSingle Crystalen_US
dc.subjectFluorescence Spectraen_US
dc.subjectDFT Calculationen_US
dc.titleSingle-step approach for synthesis of a novel tetracyclic skeleton: Investigation of X-ray analysis, fluorescence spectra, TD-DFT calculations and biological activitiesen_US
dc.typeArticleen_US

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