In present study, a series of 3-[N-(2-hydrazine-acetyl)-2-phenyl amino methyl]-1H benzimidazole derivatives (6a-6u) were designed. Molecular docking (MD) studies were conducted to select compounds with high binding affinityagainst the COX-2 enzyme (PDB ID: 3LN1). IR, 1H NMR, and mass spectral analysis characterised all test compounds. The synthesised compounds were screened for in vivo anti-inflammatory activities by the carrageenaninduced paw edema method and analgesic activities by the acetic acid-induced writhing method. Compounds 6c and6r showed the highest anti-inflammatory activities (% inhibition of 95.71% and 100% at 20 mg/kg b.w.) andanalgesic activities (86.66% and 89.33% at 100 mg/kg b.w.). All compounds were non-carcinogenic, non-toxic, andpossessed favourable drug-like properties.