Synthesis and characterization of some heteroaromatic derivatives of 3-but-2-enoyl-chromen-2-one and their potential as anti-inflammatory agents

Abstract

A novel series of chromen-2-ones containing pyrazole, isoxazole, oxazine, and thiazine substitutions have been synthesized by reacting 3-[3-(4-chloro-phenyl)-acryloyl]-chromen-2-one and 3-[3-(3-methoxy-phenyl)- acryloyl]-chromen-2-one with various cyclizing agents such as hydrazine, phenylhydrazine, urea, and thiourea. The structures of all the synthesized compounds were confirmed by the use of IR, 1H-NMR, mass spectroscopy, and elemental analysis data. All the newly synthesized compounds were evaluated for their anti-inflammatory activity at a dose of 100 mg/kg body weight in carrageenan-induced rat paw edema model. The entire series of the compounds exhibited moderate to good anti-inflammatory activity, with the percentage inhibition of edema formation ranging from 39.99 to 63.15 against the reference drug ibuprofen (100 mg/kg) that showed 78.96% inhibition at the third hour. Compounds 3a, 3c, and 3d showed good inhibitory activity, whereas compounds 3b, 3e, 3f, and 3j showed moderate inhibitory activity at the third hour. © 2013 HeteroCorporation.