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One-Pot and Green Synthesis, Anticancer Activity Assessment, and Molecular Docking Study of Novel 2-(4-Oxo-3,4-dihydroquinazolin-2-yl)-N-phenylbenzamides

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Abstract

A green protocol has been developed for the synthesis of 2-(4-oxo-3,4-dihydroquinazolin-2-yl)-N-phenylbenzamide derivatives in yields of 85–90% by a one-pot reaction of phthalic anhydride, anilines, and 2-aminobenzamides in ethanol under reflux for 90–120 min. Excellent yields, short reaction times, environmental friendliness, and mild reaction conditions are the key advantages of the developed procedure. The cytotoxicity of the synthesized compounds against A549 and HeLa cells was assessed to show good to moderate activity. The highest cytotoxicity was demonstrated by N-(4-fluorophenyl)- and N-(4-ethylphenyl)-2-(4-oxo-3,4-dihydroquinazolin-2-yl)benzamides. Molecular docking showed that both compounds effectively bound to the active site of the target human activin receptor-like kinase-2 protein through hydrogen and hydrophobic interactions.

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ACKNOWLEDGMENTS

K. Kalpana is highly grateful to the authorities of GRIET for providing research facilities.

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Authors and Affiliations

  1. Department of Humanities and Sciences (Chemistry), Gokaraju Rangaraju Institute of Engineering and Technology, Bachupally, 500090, Hyderabad, India

    K. Kalpana

  2. Department of Chemistry, Institute of Aeronautical Engineering, Dundigal, 500043, Hyderabad, India

    V. A. Rani

  3. Department of Pharmacology, SRM College of Pharmacy, SRM institute of Science and Technology, 603203, Kattankulathur Chengalpattu, India

    R. Mrinalini

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  1. K. Kalpana
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Kalpana, K., Rani, V.A. & Mrinalini, R. One-Pot and Green Synthesis, Anticancer Activity Assessment, and Molecular Docking Study of Novel 2-(4-Oxo-3,4-dihydroquinazolin-2-yl)-N-phenylbenzamides. Russ J Org Chem 59, 887–894 (2023). https://doi.org/10.1134/S1070428023050196

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