Synthesis, anti-microbial evaluation, and in silico studies of novel quinoline-isoxazole hybrids

A series of novel quinoline-isoxazole hybrids 6a-o has been synthesized via multistep synthetic approach involving hetero Diels-alder reaction strategy. The target compounds were obtained in good yield, using low-cost readily available starting materials using simple reaction conditions. The newly s...

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Bibliographic Details
Published inSynthetic communications Vol. 54; no. 18; pp. 1603 - 1619
Main Authors Mandir, Deep P., Mandir, Shivani D., Kamdar, Jignesh H., Tala, Satishkumar D.
Format Journal Article
LanguageEnglish
Published Philadelphia Taylor & Francis 16.09.2024
Taylor & Francis Ltd
Subjects
Ampicillin
Anti-fungal activity
anti-microbial activity
Antibiotics
Chemical synthesis
Cost analysis
Diels-Alder reactions
E coli
Gentamicin
isoxazole
Microorganisms
Molecular docking
NMR
Nuclear magnetic resonance
Quinoline
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Summary:A series of novel quinoline-isoxazole hybrids 6a-o has been synthesized via multistep synthetic approach involving hetero Diels-alder reaction strategy. The target compounds were obtained in good yield, using low-cost readily available starting materials using simple reaction conditions. The newly synthesized compounds were confirmed using 1 H NMR, 13 C NMR, and Mass spectroscopic analysis techniques. Further, compounds 6a-o were subjected to in vitro antimicrobial screening against various bacterial and fungal strains, such as Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Salmonella typhi, Aspergillus niger, and Candida albicans. Among these, compounds 6i, 6j, and 6 l were found most active having equally potent compared to standard drug Ampicillin and Gentamycin. Moreover, in silico studies of 6a-o with E. coli DNA gyrase through molecular docking and MD simulations showed excellent binding properties of these derivatives with protein site.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2024.2397813