In present work, a series of 1,n-bis[5-(3-methoxy-4-hydroxy-5-nitrophenyl)-1,3,4-oxadiazol-2-yl]alkanes/benzene have been synthesized. Condensation of different dihydrazides with 5-nitrovanillin gave corresponding dihydrazones. Dihydrazones on oxidative cyclization using chloramine-T yielded the corresponding bis-1,3,4- oxadiazole derivatives. Structures of newly synthesized compounds were established using FTIR, 1H NMR and elemental analysis. All compounds were screened for their anti-inflammatory activities. IC50 values reveal that newly synthesized compounds exhibit better anti-inflammatory activities. Representative samples were studied for cytotoxicity. Results of cytotoxicity reveal that compounds exhibit moderate cytotoxicity.