A novel series of tetrahydrothieno[2,3-c]pyridin-2-yl derivatives: fluorescence spectroscopy and BSA binding, ADMET properties, molecular docking, and DFT studies

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dc.authoridSERDAROGLU, Goncagul/0000-0001-7649-9168
dc.contributor.authorSerdaroglu, Goncaguel
dc.contributor.authorUludag, Nesimi
dc.contributor.authorUstun, Elvan
dc.contributor.authorColak, Naki
dc.date.accessioned2024-10-29T17:58:33Z
dc.date.available2024-10-29T17:58:33Z
dc.date.issued2023
dc.departmentTekirdağ Namık Kemal Üniversitesi
dc.description.abstractIn this study, a series of substituted tetrahydrothieno[2,3-c]pyridin-2-yl (THTP) derivatives, i.e., C1-C3 and N1-N3, was synthesized in one step using 2-amino-5,5,7,7-tetramethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carbonitrile with two different adjacent chloro- and nitro-substituted groups. Specifically, with a nitrile group on the thiophene structure, six new THTP (C1-C3 and N1-N3)-bearing electron-donating-electron-withdrawing moieties were designed with various pharmacological properties. For the first time in the literature, the synthesis of these target pharmaceutical products was carried out in less steps with high efficiency. Specifically, the notable features of this protocol are its simplicity and high reaction yields. Furthermore, spectroscopic methods were used to verify the structures of all the synthesized compounds (FT-IR, UV, H-1 NMR, and C-13 NMR). Additionally, the binding properties of the molecules with serum albumin were analyzed as a function of concentration and temperature and in the presence of Mg2+, Zn2+, and Ca2+. Moreover, molecular docking calculations were performed against bovine serum albumin, human leukemia inhibitory factor, and DNA. Also, DFT and TD-DFT computational studies were performed at the B3LYP/6-311G** level for structural and spectroscopic confirmation of compounds C1-C3 and N1-N3, and their possible reactivity features were evaluated via FMO frontier molecular orbital and NBO natural bond orbital analyses. Further, their physicochemical properties such as lipophilicity and water solubility, in addition to ADMET properties were estimated and evaluated. Considering the results obtained from the experiments and computations, it is hoped that this work will be a useful guide for future research on drug design.
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [112T503]
dc.description.sponsorshipFinancial support for this research from the Scientific and Technological Research Council of Turkey (TUBITAK Project No. 112T503). The authors thank Namik Kemal University for the analysis of our article structure. All calculations have been carried out at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure).
dc.identifier.doi10.1039/d3nj01648j
dc.identifier.endpage11963
dc.identifier.issn1144-0546
dc.identifier.issn1369-9261
dc.identifier.issue25en_US
dc.identifier.scopus2-s2.0-85163301439
dc.identifier.scopusqualityQ2
dc.identifier.startpage11945
dc.identifier.urihttps://doi.org/10.1039/d3nj01648j
dc.identifier.urihttps://hdl.handle.net/20.500.11776/14383
dc.identifier.volume47
dc.identifier.wosWOS:001011181800001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherRoyal Soc Chemistry
dc.relation.ispartofNew Journal of Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectBovine Serum-Albumin
dc.subjectLeukemia-Inhibitory Factor
dc.subjectPlasma-Protein Binding
dc.subjectDrug Discovery
dc.subjectBiological Evaluation
dc.subjectEfficient Synthesis
dc.subjectSolubility
dc.subjectPrediction
dc.subjectBioavailability
dc.subjectOptimization
dc.titleA novel series of tetrahydrothieno[2,3-c]pyridin-2-yl derivatives: fluorescence spectroscopy and BSA binding, ADMET properties, molecular docking, and DFT studies
dc.typeArticle

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