Synthesis, Antibacterial Activity, and Molecular Docking Study of 3-Phenylquinazolin-4(3H)-one Derivatives

A novel economic DMSO-assisted methodology for synthesizing 3-phenylquinazolin-4(3 H )-one derivatives from easily accessible 2-aminobenzoic acids and anilines in the presence of K 2 S 2 O 8 as an additive and molecular iodine as a catalyst. In this reaction, DMSO acted as both solvent and one-carbo...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2023-09, Vol.59 (9), p.1591-1597
Main Authors: Rather, R. A., Ara, T.
Format: Article
Language:English
Subjects:
Aniline
Carbonic anhydrase
Chemical synthesis
Chemistry
Chemistry and Materials Science
E coli
Iodine
Molecular docking
NMR
Nuclear magnetic resonance
Organic Chemistry
Potassium persulfate
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Summary:A novel economic DMSO-assisted methodology for synthesizing 3-phenylquinazolin-4(3 H )-one derivatives from easily accessible 2-aminobenzoic acids and anilines in the presence of K 2 S 2 O 8 as an additive and molecular iodine as a catalyst. In this reaction, DMSO acted as both solvent and one-carbon synthon. The compounds were characterized by 1 H and 13 C NMR, HRMS, LC/MS, and elemental analysis and were tested against several bacterial and fungal strains. 7-Chloro-3-phenylquinazolin-4(3 H )-one showed significant antibac­terial activity against E. coli with IC 50 and MIC values of 18.5±4.0 and 38 μg/mL, respectively, and 6-bromo-3-(2-fluorophenyl)quinazolin-4(3 H )-one was active against S. aureus with IC 50 and MIC values of 16.0±1.9 and 36 μg/mL, respectively. None of the compounds inhibited C. albicans . Molecular docking study was performed on 6-bromo-3-(3-methylphenyl)quinazolin-4(3H)-one against human carbonic anhydrase IX.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428023090178