Synthesis, characterization, antimicrobial activity, and QSAR studies of some new 6-substituted phenyl 3-(4-chlorophenyl)-3a,4,8,8a-tetrahydro-[1,3,2]dioxaborepino [5,6-d]isoxazoles

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dc.authoridSahin, Onur/0000-0003-3765-3235
dc.contributor.authorPir, Meryem
dc.contributor.authorAgirbas, Hikmet
dc.contributor.authorBudak, Fatma
dc.contributor.authorSahin, Onur
dc.date.accessioned2025-03-23T19:47:10Z
dc.date.available2025-03-23T19:47:10Z
dc.date.issued2017
dc.departmentSinop Üniversitesi
dc.description.abstract3-(4-Chlorophenyl)-3a,4,8,8a-tetrahydro-[1,3,2]dioxaborepino[5,6-d] isoxazoles were synthesized from the reaction of (3-(4-chlorophenyl)-4,5-dihydroisoxazole-4,5-diyl) dimethanol with substituted phenylboronic acids. Crystal structure of 1-(4-(3-(4-chlo rophenyl)-3a,4,8,8a-tetrahydro-[1,3,2]dioxaborepino[5,6-d] isoxazol-6-yl) phenyl) ethanone was studied and the values of selected bond distances (angstrom), bond angles (degrees), and dihedral angles (degrees) were found in agreement with the calculated (DFT, B3LYP/6-311++G(d,p)) values. Antimicrobial activity of these new compounds was also studied against a panel of microorganisms including Staphylococcus aureus, Enterococcus faecalis, Pseudomonas aeruginosa, Escherichia coli, Streptococcus mutans, and Candida albicans. Most of the dioxaborepines exhibited fair activities against these microorganisms. The pMIC values of the compounds were first correlated with Hammett polar substituent constant (sigma) together with lipophilic constant (pi) and statistically significant 2D correlations were obtained. In addition, the pMIC values of the compounds were correlated with some theoretical descriptors and fair 2D-QSAR models with clogP, SAA, and mu as independent variables were obtained.
dc.identifier.doi10.1002/hc.21363
dc.identifier.issn1042-7163
dc.identifier.issn1098-1071
dc.identifier.issue2
dc.identifier.scopus2-s2.0-85010737655
dc.identifier.scopusqualityQ4
dc.identifier.urihttps://doi.org/10.1002/hc.21363
dc.identifier.urihttps://hdl.handle.net/11486/7301
dc.identifier.volume28
dc.identifier.wosWOS:000397847100005
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherWiley-Hindawi
dc.relation.ispartofHeteroatom Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectSubstituent Constants
dc.subjectBoron
dc.titleSynthesis, characterization, antimicrobial activity, and QSAR studies of some new 6-substituted phenyl 3-(4-chlorophenyl)-3a,4,8,8a-tetrahydro-[1,3,2]dioxaborepino [5,6-d]isoxazoles
dc.typeArticle

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