Synthesis of highly potent and enhanced safety profiled antiinflammatory drugs has become a challenging task in the drug discovery process. A library of warfarin analogue 3-(4‑hydroxy-2-oxo-2H-chromen-3-yl)-3-arylpropanoic acid derivatives have been synthesised and their structures were established by availing different analysis techniques. The invitro COX-1/COX-2 study revealed the effective potency of the selective compounds 2b(IC50=180.45 µl/ml), 2c(IC50=21.03 µl/ml) and 2f(IC50=120.45 µl/ml) against COX-2 compared to reference drug aspirin (IC50=121.60 µl/ml). Compound 2c is more selective towards COX-2 with a high selective index of 7.42 than standard aspirin with a selective index of 4.14. Further, the target molecules were assessed for their antiinflammatory activity against MMP2 and MMP9, the results revealing a high percentage of inhibition. While, protein denaturation study displayed high potency of the compounds 2a (IC50=13.32 µg/ml), 2 g (IC50=11.14 µg/ml) and 2l (IC50=4.71 µg/ml) as compared with aspirin (IC50=13.42 µl/ml). The docking studies were established to understand the structural features responsible for biological activity and the outcome of the docking studies are indeed following the experimental results.