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

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dc.contributor.authorÇevik, Ulviye Acar
dc.contributor.authorÇelik, İsmail
dc.contributor.authorIşık, Ayşen
dc.contributor.authorGül, Ülküye Dudu
dc.contributor.authorBayazıt, Gizem
dc.contributor.authorBostancı, Hayrani Eren
dc.contributor.authorÖzkay, Yusuf
dc.contributor.authorKaplancıklı, Zafer Asım
dc.date.accessioned2023-04-11T13:06:09Z
dc.date.available2023-04-11T13:06:09Z
dc.date.issued01.09.2022tr
dc.departmentEczacılık Fakültesitr
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-(4cycylohexylpiperazin-1-yl)-2-((1-methyl-1H-tetrazol-5-yl)thio)ethan-1-one (2b) (MIC ¼ 7.81 mg/mL) and 1-(4-(4-chlorobenzyl)piperazin-1-yl)-2-((1-methyl-1H-tetrazol-5-yl)thio)ethan-1-one (2f) (MIC ¼ 3.90 mg/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 mg/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 mg/mL. All the derivatives were efficiently synthesized by a twostep process. The structure of the newly synthesized compounds was elucidated by their 13 C 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. 1 HNMR,tr
dc.identifier.citationUlviye Acar C¸evika , Ismail Celikb , Ays¸en Is¸ıkc , Ulk € uye Dudu G € ul € d , Gizem Bayazıt e , Hayrani Eren Bostancı f , Yusuf Ozkay € a , and Zafer Asım Kaplancıklı a a Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, Eskis¸ehir, Turkey; b Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Erciyes University, Kayseri, Turkey; c Department of Biochemistry, Faculty of Science, Selc¸uk University, Konya, Turkey; d Department of Bioengineering, Faculty of Engineering, Bilecik Seyh Edebali University, Bilecik, Turkey; e Department of Biotechnology, Institute of Graduate Studies, Bilecik Seyh Edebali University, Bilecik, Turkey; f Department of Biochemistry, Faculty of Pharmacy, Sivas Cumhuriyet University, Sivas, Turkeytr
dc.identifier.doi10.1080/10426507.2022.2117812en_US
dc.identifier.endpage144tr
dc.identifier.issue2tr
dc.identifier.scopus2-s2.0-85138009640en_US
dc.identifier.scopusqualityN/A
dc.identifier.startpage137tr
dc.identifier.urihttps://hdl.handle.net/20.500.12418/13534
dc.identifier.volume198tr
dc.identifier.wosWOS:000849766100001en_US
dc.identifier.wosqualityQ4
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherTaylor & Francistr
dc.relation.ispartofPhosphorus, Sulfur, and Silicon and the Related Elementsen_US
dc.relation.publicationcategoryUluslararası Hakemli Dergide Makale - Kurum Öğretim Elemanıtr
dc.rightsinfo:eu-repo/semantics/openAccesstr
dc.subjectTetrazole; antimicrobial; candida; molecular docking; 14a-demethylasetr
dc.titleSynthesis, and docking studies of novel tetrazole S-alkyl derivatives as antimicrobial agentsen_US
dc.typeArticleen_US

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