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(3H)-one derivatives from easily accessible 2-aminobenzoic acids and anilines in the presence of K2S2O8 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 H-1 and C-13 NMR, HRMS, LC/MS, and elemental analysis and were tested against several bacterial and fungal strains. 7-Chloro-3-phenylquinazolin-4(3H)-one showed significant antibacterial activity against E. coli with IC50 and MIC values of 18.5 +/- 4.0 and 38 mu g/mL, respectively, and 6-bromo-3-(2-fluorophenyl)quinazolin-4(3H)-one was active against S. aureus with IC50 and MIC values of 16.0 +/- 1.9 and 36 mu g/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.