Synthesis of thiophene derivatives: Substituent effect, antioxidant activity, cyclic voltammetry, molecular docking, DFT, and TD-DFT calculations

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dc.authoridKUMAR, Dr. P. RAJ/0000-0003-1013-8786
dc.authoridSERDAROGLU, Goncagul/0000-0001-7649-9168
dc.authoriduludag, Nesimi/0000-0002-2819-3612
dc.authorwosidKUMAR, Dr. P. RAJ/AFS-5942-2022
dc.authorwosidSerdaroğlu, Goncagül/ADT-1750-2022
dc.contributor.authorUludağ, Nesimi
dc.contributor.authorSerdaroğlu, Goncagül
dc.contributor.authorSugumar, Paramasivam
dc.contributor.authorRajkumar, Parthasarathi
dc.contributor.authorÇolak, Naki
dc.contributor.authorErçağ, Erol
dc.date.accessioned2023-04-20T08:04:15Z
dc.date.available2023-04-20T08:04:15Z
dc.date.issued2022
dc.departmentFakülteler, Fen Edebiyat Fakültesi, Kimya Bölümü
dc.description.abstractThe efficient pathway 6-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate derivatives have been synthesized. Due to the promising biochemical reactivity, the bioactive agent synthesis in the frame of the thiophene moiety is one of the main objectives of the contemporary scientific disciplines. The structures of all the presently synthesized compounds were confirmed using spectroscopic methods (UV-vis, FT-IR, H-1 NMR, C-13 NMR). The cyclic voltammetry (CV) of three compounds (1-3) was performed using a bare ITO electrode and a Nafion modified ITO (Indium Tin Oxide) electrode. The antioxidant properties of these compounds were explored by the CUPRAC method and TEAC (Trolox equivalent total antioxidant capacity) coefficients revealed that the antioxidant capacity of the compounds was ranking as follows: compound 2 (C-2) > compound 3 (C-3) > compound 1 (C-1). The docking studies displayed that compound 1 was the most active compound against Escherichia coli thymidylate synthase (TS). The TD-DFT calculations displayed that two observed peaks on the UV-vis spectra of the thiophenes were related to the n & nbsp;-> pi* and pi & nbsp;-> pi* transitions. Also, NBO (Natural Bond Orbital) analysis indicated that the resonance interactions (n & nbsp;-> pi* and pi & nbsp;-> pi*) in the ground state of all compounds had an essential role in the decreasing of the stabilization energy. The antioxidant activity and molecular docking results were supported by the electrodonating power and hardness indexes in addition to the NBO results. (C)& nbsp;2022 Elsevier B.V. All rights reserved.
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [112T503]; Sivas Cumhuriyet University scientific research projects department [CUBAP: E G?T-090]
dc.description.sponsorship& nbsp;We are grateful to the Scientific and Technological Research Council of Turkey (TUBITAK Project No. 112T503) for financial sup-port and by the Sivas Cumhuriyet University scientific research projects department (Project No: CUBAP: E G?T-090) . All calculations have been carried out at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure) .
dc.identifier.doi10.1016/j.molstruc.2022.132607
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85124869581
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2022.132607
dc.identifier.urihttps://hdl.handle.net/20.500.11776/11053
dc.identifier.volume1257
dc.identifier.wosWOS:000789877800008
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorUludağ, Nesimi
dc.institutionauthorErçağ, Erol
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectThiophene
dc.subjectCyclic Voltammetry
dc.subjectAntioxidant Activity
dc.subjectMolecular Docking
dc.subjectDft Calculations
dc.subjectBinding
dc.subjectNmr
dc.subjectNbo
dc.subjectFmo
dc.titleSynthesis of thiophene derivatives: Substituent effect, antioxidant activity, cyclic voltammetry, molecular docking, DFT, and TD-DFT calculations
dc.typeArticle

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