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

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Abstract

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 1H and 13C 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 μg/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 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.

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CONFLICT OF INTEREST

The authors declare no conflict of interest.

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ACKNOWLEDGMENTS

The authors thank the National Institute of Technology Srinagar for financial support of this study and the director, Prof. R. Sehgal for his assistance.

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This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

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  1. National Institute of Technology Srinagar, Hazratbal, 190006, Srinagar, Jammu & Kashmir, India

    R. A. Rather & T. Ara

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Rather, R.A., Ara, T. Synthesis, Antibacterial Activity, and Molecular Docking Study of 3-Phenylquinazolin-4(3H)-one Derivatives. Russ J Org Chem 59, 1591–1597 (2023). https://doi.org/10.1134/S1070428023090178

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