Molecular stabilities, conformational analyses and molecular docking studies of benzimidazole derivatives bearing 1,2,4-triazole as EGFR inhibitors

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dc.authoridKARAYEL, ARZU / 0000-0002-3369-8690
dc.contributor.authorKarayel, Arzu
dc.date.accessioned2021-11-01T15:05:27Z
dc.date.available2021-11-01T15:05:27Z
dc.date.issued2021
dc.department[Belirlenecek]
dc.description.abstractA detailed study of the tautomeric properties, the conformations, and the mechanism behind the anti-cancer properties of 5-{[2-(4-methoxyphenyl)-1H-benzimidazol-1-yl]methyl}-4-ethyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (1), 2-(4-chlorophenyl) (2), 2-phenyl (3), 2-(3,4-dibenzyloxyphenyl) (4), and 2-(4-methoxyphenyl); 4-[2-(piperidin-1-yl)ethyl] (5) has been conducted using density functional theory and molecular docking. The most stable states of all the structures are shown to be in the thione form. The scans of the compounds point out two conformers at PES, one of two conformers for molecule 1 corresponds to X-ray geometry, being the lowest energy state. Current molecules (1, 2, 3, and 5) have one inter-molecular hydrogen bond between NH atom of triazole ring and =O atom in residue ARG817 of the EGFR binding pocket, while compound 4 has different type inter-molecular hydrogen bond which is between N atom in benzimidazole ring and H atom of NH3 in residue LYS721. Off all hydrogen bonds, that of 5 is the strongest one with 2.26 angstrom. Compound 4 has shown the best binding affinity with -10.0 kcal/mol. This compound is the most active compound regarding to the potential anti-cancer activity.
dc.description.sponsorshipHitit UniversityScientific Research Unit (BAP) [FEF19004.17.001]en_US
dc.description.sponsorshipThe author acknowledges Hitit UniversityScientific Research Unit (BAP) with project number FEF19004.17.001. I thank to Prof. Dr. Gulgun Ayhan Kilcigil and Dr. Ismail Celik for the synthesis of compounds and their valuable supports. I also thank to Assoc. Prof. Dr. Sevil Ozkinali for the useful comments. The numerical calculations reported in this paper were partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).en_US
dc.identifier.doi10.1007/s11224-021-01760-8
dc.identifier.endpage1259en_US
dc.identifier.issn1040-0400
dc.identifier.issn1572-9001
dc.identifier.issue3en_US
dc.identifier.scopus2-s2.0-85102525079
dc.identifier.scopusqualityQ2
dc.identifier.startpage1247en_US
dc.identifier.urihttps://doi.org/10.1007/s11224-021-01760-8
dc.identifier.urihttps://hdl.handle.net/11491/7281
dc.identifier.volume32en_US
dc.identifier.wosWOS:000627656800001
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthor[Belirlenecek]
dc.language.isoen
dc.publisherSpringer/Plenum Publishers
dc.relation.ispartofStructural Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectBenzimidazole bearing 1en_US
dc.subject2en_US
dc.subject4-triazoleen_US
dc.subjectThione-thiol tautomerismen_US
dc.subjectEGFRen_US
dc.subjectDFTen_US
dc.subjectMolecular dockingen_US
dc.subjectConformational analysisen_US
dc.titleMolecular stabilities, conformational analyses and molecular docking studies of benzimidazole derivatives bearing 1,2,4-triazole as EGFR inhibitors
dc.typeArticle

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