Abstract: A novel series of o-benzoyl benzoic acid based 1,3,4-oxadiazoles were prepared and subjected to anti-inflammatory, analgesic activity as well as molecular docking studies to target cyclooxygenase-2 enzyme.1,3,4-Oxadiazole derivatives were screened for anti-inflammatory activity in carrageenan-induced rat paw edema and analgesic activity by tail immersion method. In synthesized compounds, the free carboxylic group, which is responsible for gastric side effects, was derivatized by heterocyclic 1,3,4-oxadiazole bioactive core, which showed good interaction with COX-2 receptor with good docking score. Among all thesynthesized compound having m-methoxy-p-hydroxy have emerged out as potential COX-2 inhibitor.