Synthesis and pharmacological investigations of novel 2-phenylquinazolin-4(3H)-one derivatives

A series of novel 2-phenyl-3-(4-(5-substitutedphenylisoxazol-3-yl)phenyl)quinazolin-4(3H)-one 5a–5o were designed and synthesized from anthranilic acid. All the synthesized compounds were characterized by FT-IR, 1H NMR, mass spectroscopy, and bases of elemental analysis. Tail-flick technique, carrageenan-induced foot paw edema test, and agar streak dilution test were performed for screening analgesic, anti-inflammatory and in vitro antimicrobial activity, respectively. Moreover, all compounds were examined for its ulcerogenicity. Results of biological studies revealed that all title compounds exhibited mild to good analgesic, anti-inflammatory, and antimicrobial activity with low to moderate ulcer index. The relationship between the functional group variation and the biological activity of the evaluated compounds was discussed. Out of fifteen title compounds, 2-phenyl-3-(4-(5-(4-(trifluoromethyl)phenyl)isoxazol-3-yl)phenyl) quinazolin-4(3H)-one 5f was found to be the most active compound.