In search of non-purine based xanthine oxidase inhibitors, a series of benzochromone derivatives was synthesized via Vilsmeier-Haack reaction. All the derivatives were evaluated for in vitro xanthine oxidase inhibition using spectrophotometric assay. Among the series of 14 compounds,CK-10 displayed strong inhibition of xanthine oxidase enzyme (IC50 = 0.65 μM).Enzyme kinetic study carried out to determine the type of inhibition, revealed that compound CK-10 was a mixed type inhibitor. Molecular modelling study was also performed to investigate the binding interactions between xanthine oxidase and the most potent inhibitor, CK-10. Furthermore, compliance of some potent benzochromone derivatives to the Lipinski rule was also calculated.