Synthesis, and docking studies of novel tetrazole-S-alkyl derivatives as antimicrobial agents

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dc.contributor.authorAcar Çevik, Ulviye
dc.contributor.authorCelik, Ismail
dc.contributor.authorIşık, Ayşen
dc.contributor.authorGül, Ülküye Dudu
dc.contributor.authorBayazıt, Gizem
dc.contributor.authorBostancı, Hayrani Eren
dc.contributor.authorÖzkay, Yusuf
dc.date.accessioned2025-05-04T16:42:00Z
dc.date.available2025-05-04T16:42:00Z
dc.date.issued2023
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractA series of novel tetrazole-S-alkyl-piperazine derivatives were synthesized and evaluated for their antifungal activity against C. albicans (ATCC 24433), C. krusei (ATCC 6258) and C. parapsilosis (ATCC 22019) and antibacterial activity against E. coli (ATCC 25922), S. marcescens (ATCC 8100), K. pneumoniae (ATCC 13883), P. aeruginosa (ATCC 27853), E. faecalis (ATCC 2942), B. subtilis (ATCC), S. aureus (ATCC 29213), S. epidermidis (ATCC 12228). Among the synthesized compounds, 1-(4-cycylohexylpiperazin-1-yl)-2-((1-methyl-1H-tetrazol-5-yl)thio)ethan-1-one (2b) (MIC = 7.81 µg/mL) and 1-(4-(4-chlorobenzyl)piperazin-1-yl)-2-((1-methyl-1H-tetrazol-5-yl)thio)ethan-1-one (2f) (MIC = 3.90 µg/mL) displayed significant antifungal activity and compared to reference drugs voriconazole and fluconazole. Besides, compound 2b has showed also higher antibacterial activity against E. faecalis (ATCC 2942) as a reference drug azithromycin, with a MIC value of 3.90 µg/mL, and compound 2d was found to be effective against S. epidermidis (ATCC 12228) as the same reference drug, with a MIC value of 7.81 µg/mL. All the derivatives were efficiently synthesized by a two-step process. The structure of the newly synthesized compounds was elucidated by their 1H NMR, 13C NMR, LC-MS/MS, and elemental analysis. In this study, the detailed synthesis, spectroscopic and biological evaluation data are reported. Molecular docking studies of all compounds were performed with the sterol 14-alpha demethylase enzyme of C. albicans, the target enzyme of azole antifungal drugs. © 2022 Taylor & Francis Group, LLC.
dc.description.sponsorshipAnkara University-Scientific Research Unit, (BAP-21B0237004)
dc.identifier.doi10.1080/10426507.2022.2117812
dc.identifier.endpage144
dc.identifier.issn1042-6507
dc.identifier.issue2
dc.identifier.scopus2-s2.0-85138009640
dc.identifier.scopusqualityQ3
dc.identifier.startpage137
dc.identifier.urihttps://doi.org/10.1080/10426507.2022.2117812
dc.identifier.urihttps://hdl.handle.net/20.500.12418/35030
dc.identifier.volume198
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherTaylor and Francis Ltd.
dc.relation.ispartofPhosphorus, Sulfur and Silicon and the Related Elements
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_Scopus_20250504
dc.subject14α-demethylase
dc.subjectantimicrobial
dc.subjectcandida
dc.subjectmolecular docking
dc.subjectTetrazole
dc.titleSynthesis, and docking studies of novel tetrazole-S-alkyl derivatives as antimicrobial agents
dc.typeArticle

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