Design, synthesis, characterization, and theoretical calculations, along with in silico and in vitro antimicrobial proprieties of new isoxazole-amide conjugates

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dc.authoridChalkha, Mohammed/0000-0002-9400-2183
dc.authoridAlanazi, Mohammed/0000-0002-0483-8113
dc.contributor.authorBarghady, Najoua
dc.contributor.authorAssou, Soumia Ait
dc.contributor.authorEr-Rajy, Mohammed
dc.contributor.authorBoujdi, Khalid
dc.contributor.authorArzine, Aziz
dc.contributor.authorRhazi, Yassine
dc.contributor.authorTuezuen, Burak
dc.date.accessioned2025-05-04T16:45:57Z
dc.date.available2025-05-04T16:45:57Z
dc.date.issued2024
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractFunctionalized isoxazoles provide valuable structural motifs, opening up a wide range of uses in the medicinal, pharmacological, and pharmaceutical fields. Within this scope, an efficient approach has been adopted to synthesize a novel series of functionalized isoxazole derivatives, starting from aza-aurone, providing reproducible access to the desired isoxazoles in excellent yields. All synthesized compounds were structurally elucidated through the use of various spectroscopic techniques and mass spectrometry. The derivatives generated were screened for their antimicrobial potential against the fungus Candida albicans as well as three bacterial strains. The results show that almost all of the tested isoxazole derivatives were found to be significantly potent against the fungus C. albicans. The functionalized isoxazoles were also computed using the Gaussian software package with the 6-31++G(d,p) basis set at B3LYP, HF, and M062X levels, and their chemical activities were compared. Moreover, the molecular docking studies of tested isoxazole compounds were performed against the C. albicans receptor. The results suggest that the newly synthesized compounds exhibit docking scores ranging from -10.29 to -15.08 kcal/mol, revealing a high affinity for the target enzyme (5V5Z). Lastly, drug similarity studies and ADMET (absorption, distribution, metabolism, excretion, and toxicity) properties assessments indicate that isoxazole derivatives have favorable absorption, distribution, and metabolism properties associated with a proven lack of toxicity.
dc.description.sponsorshipKing Saud University, Riyadh, Saudi Arabia [RSPD2024R628]
dc.description.sponsorshipThe authors extend their appreciation to the Researchers Supporting Project number (RSPD2024R628), King Saud University, Riyadh, Saudi Arabia, for supporting this research. The numerical calculations reported in this paper were fully/partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).
dc.identifier.doi10.1515/chem-2024-0109
dc.identifier.issn2391-5420
dc.identifier.issue1
dc.identifier.scopus2-s2.0-85208986995
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1515/chem-2024-0109
dc.identifier.urihttps://hdl.handle.net/20.500.12418/35300
dc.identifier.volume22
dc.identifier.wosWOS:001344262300001
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherDe Gruyter Poland Sp Z O O
dc.relation.ispartofOpen Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WOS_20250504
dc.subjectsynthesis
dc.subjectaza-aurones
dc.subjectspiro-isoxazolines
dc.subjectisoxazole
dc.subjectamide
dc.subjectantimicrobial activity
dc.subjectmolecular docking studies
dc.subjectADMET property
dc.titleDesign, synthesis, characterization, and theoretical calculations, along with in silico and in vitro antimicrobial proprieties of new isoxazole-amide conjugates
dc.typeArticle

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