Synthesis, characterization, theoretical studies and antimicrobial activity of novel 1-(2-hydroxy-4-propoxy-3-propylphenyl)ethanones bearing thiotetrazole

Basit Öğe Kaydı
dc.authoridDilek, Gulay/0000-0001-6562-2554
dc.contributor.authorDisli, Ali
dc.contributor.authorYucesoy, Esin Eylem
dc.contributor.authorErdogdu, Yusuf
dc.contributor.authorGulluoglu, Mehmet Tahir
dc.contributor.authorOzturk, Ali
dc.contributor.authorDilek, Gulay
dc.date.accessioned2024-11-07T13:34:30Z
dc.date.available2024-11-07T13:34:30Z
dc.date.issued2021
dc.departmentNiğde Ömer Halisdemir Üniversitesi
dc.description.abstractWe report herein a joint experimental and theoretical investigation on the novel 1-(2-hydroxy-4-propoxy-3-propylphenyl)ethanone bearing 1-propyl-1H-tetrazol-5-thiol and 2-propyl-2H-tetrazole-5-thiol pharmacophores. In the experimental studies, 1-[4-(34(1-propyl-1H-tetrazol-5-y1)thio)propoxy)2-hydroxy-3-propylphenyliethanone and 1-[4-(34(2-propyl-2H-tetrazol-5-yl)thio)propoxy)-2-hydroxy-3propylphenyliethanone were synthesized and characterized by ATR-FTIR, (1) H NMR, C-13-APT, and HRMS. In the theoretical studies, the most stable conformations, vibrational and NMR spectra of these compounds were predicted by Quantum chemical calculations. Quantum chemical calculations were performed using the B3LYP functional with 3-21 G, and 6-311++G(d,p) basis sets. All quantum chemical calculations were utilized Gaussian 16 software. While torsional barriers of the compounds were determined by B3LYP/3-21 G, their geometry optimizations were performed by B3LYP functional with 3-21 G, and 6-311++G(d,p) basis sets. The harmonic vibrational frequencies, potential energy distribution (PED) and infrared intensities were predicted using the B3LYP/6-311++G(d,p). Theoretically predicted vibrational frequencies were compared with experimental results. Predicted NMR chemical shifts were obtained by the GIAO method using the B3LYP/6-311++G(d,p). The (1) H and (13) C experimental chemical shifts are consistent with the theoretical NMR chemical shift values. Antimicrobial activities of the title compounds were investigated against five bacterial strains (Staphylococcus aureus, Staphylococcus epidennidis, Escherichia coli, Pseudomonas aeruginosa, Stenotrophomonas maltophilia) and two fungal strains (Candida albicans, Aspergillus fumigatus). The compounds showed good antimicrobial activity and inhibited all tested bacteria and fungi. (C) 2021 Elsevier B.V. All rights reserved.
dc.identifier.doi10.1016/j.molstruc.2021.130818
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85108277210
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2021.130818
dc.identifier.urihttps://hdl.handle.net/11480/16026
dc.identifier.volume1242
dc.identifier.wosWOS:000675890800003
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_20241106
dc.subjectThiotetrazole
dc.subjectAlkyl tetrazole
dc.subjectAntimicrobial activity
dc.subjectConformational analysis
dc.subjectDFT
dc.titleSynthesis, characterization, theoretical studies and antimicrobial activity of novel 1-(2-hydroxy-4-propoxy-3-propylphenyl)ethanones bearing thiotetrazole
dc.typeArticle

Dosyalar

Koleksiyon

WoS İndeksli Yayınlar Koleksiyonu
Scopus İndeksli Yayınlar Koleksiyonu