The study focuses on the synthesis and evaluation of 1-(2-(1-benzoyl-3 (thiophen-2-yl)- 1H-pyrazol-4-yl)-5-substituted-1,3,4-oxadiazol-3(2H) yl)ethanone derivatives (8a-g) for their anti-inflammatory properties and drug-like behavior. Spectral studies confirmed the structural integrity of the compounds through characteristic IR, 1H NMR, and 13C NMR signals. The HRBC membrane stabilization assay revealed significant anti-inflammatory activity, particularly for compounds 8g (IC50 107.54 ± 0.06 µg/ml) and 8f (IC50 145.75 ± 0.05 µg/ml), comparable to the standard drug Diclofenac Sodium (DFS). Docking studies showed strong binding affinities to COX-1 and COX-2 enzymes, with compound 8f displaying the best binding affinity for COX-1 (-8.5) and compound 8e for COX-2 (-7.4). ADME analysis indicated that all compounds adhered to Lipinski’s Rule of Five, with favorable pharmacokinetic parameters, including appropriate lipophilicity, water solubility, and cell permeability. These findings suggest that the synthesized 1,3,4-oxadiazole derivatives exhibit potential as effective anti inflammatory agents with suitable drug-like properties, warranting further development and clinical exploration.