Fluorobenzylidene-1,2,4-triazol-3-one Derivatives: Synthesis, Characterization, Antimicrobial Activity, and Molecular Docking Study

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dc.contributor.authorSuleymanoglu, N.
dc.contributor.authorCobuloglu, S. Utas
dc.contributor.authorCelik, F.
dc.contributor.authorUnver, Y.
dc.contributor.authorUstabas, R.
dc.contributor.authorGuler, H. I.
dc.contributor.authorDirekel, S.
dc.date.accessioned2026-06-19T06:39:20Z
dc.date.available2026-06-19T06:39:20Z
dc.date.issued2025
dc.departmentMalatya Turgut Özal Üniversitesi
dc.description.abstractA series of three fluorobenzylidene-1,2,4-triazol-3-one derivatives & horbar;(E)-4-[(2-fluorobenzylidene)amino]- (1), (E)-4-[(3-fluorobenzylidene)amino]- (2), and (E)-4-[(4-fluorobenzylidene)amino]-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (3)& horbar;were synthesized and characterized by FTIR and 1H and 13C NMR spectroscopy. Of the three synthesized isomeric (E)-4-(fluorobenzylideneamino)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one derivatives, isomers 1 and 2 are novel compounds, and compound 3 is previously known. A theoretical study was performed using the DFT/B3LYP/6-311++G(d,p) method. The molecular structures of compounds 1-3 were optimized, and their structural parameters were determined. Experimental FT-IR and NMR data were compared with calculated values, which confirmed the molecular structures and supported the experimental findings. The antibacterial and leishmaniacidal activities of compounds 1-3 were evaluated by the microdilution assay. Streptococcus pneumoniae was the most susceptible bacterium, while compound 2 was less effective against the tested bacteria than the other derivatives. Molecular docking analysis identified key molecular interactions responsible for the antileishmanial activity of compound 1, demonstrating a high binding affinity for Trypanothione reductase (TRe).
dc.identifier.doi10.1134/S1070428025600238
dc.identifier.endpage1491
dc.identifier.issn1070-4280
dc.identifier.issn1608-3393
dc.identifier.issue8
dc.identifier.scopus2-s2.0-105018643599
dc.identifier.scopusqualityQ4
dc.identifier.startpage1479
dc.identifier.urihttps://doi.org/10.1134/S1070428025600238
dc.identifier.urihttps://hdl.handle.net/20.500.12899/5541
dc.identifier.volume61
dc.identifier.wosWOS:001590962900015
dc.identifier.wosqualityQ4
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherPleiades Publishing Ltd
dc.relation.ispartofRussian Journal of Organic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20260612
dc.subjectFluorobenzylidene-1,2,4-Triazol-3-One Derivatives
dc.subjectIr And Nmr Spectroscopy
dc.subjectDft
dc.subjectAntibacterial And Leishmaniacidal Activities
dc.subjectIn Silico Study
dc.titleFluorobenzylidene-1,2,4-triazol-3-one Derivatives: Synthesis, Characterization, Antimicrobial Activity, and Molecular Docking Study
dc.typeArticle

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