In this study, 24 new benzimidazole-oxadiazole hybrids were designed and synthesized as anti-inflammatory agents. It was measured their stabilizing potentials against heat-induced human erythrocyte membrane hemolysis for anti-inflammatory activity. Compound 5 w bearing cyclohexyl as R-2 group at the 2(nd) position of oxadiazole ring and 3,4-dimethoxy phenyl at the 2(nd) position of benzimidazole showed the highest membrane stabilizing activity with IC50= 0.50 mM. Antioxidant activity screening of compounds synthesized by ABTS and DPPH radical scavenging assay methods was performed. Molecular docking studies of all compounds were performed against COX-1 and COX-2 with Glide XP. Moreover, to examine the protein-ligand stability of the most active compound 5 w, molecular dynamics simulations of 100 ns duration were performed with COX-1 and COX-2 using Gromacs.