Novel bis(1,3,4-oxadiazole) derivatives 2( a–h) and 3,5-bis(substituted)pyrazoles 3( a, b, d–i) and isoxazoles 4( a–c) were synthesized and evaluated for their antioxidant and antibacterial activities and results were compared with standard. Two series of five membered heterocyclic bis(1,3,4-oxadiazole) derivatives 2( a– h) and 3,5-bis(substituted)pyrazoles, isoxazoles 3( a, b, d– i), 4( a– c) were synthesized via oxidative cyclization of some diaroylhydrazones using chloramine-T and cyclocondensation reaction with hydrazine hydrate and hydroxylamine hydrochloride, respectively. The newly synthesized compounds were screened for antioxidant and anti-microbial activities. Compounds 2( b), 3( b), and 4( a) showed higher antioxidant activity at 10 μg/ml while compounds 2( a), 3( a), 3( f), and 4( a) exhibited better anti-microbial activity at 100 μg/ml compared with standard vitamin C and ciprofloxacin, respectively. Structures of newly synthesized compounds were confirmed by elemental analysis and spectral IR, 1H NMR, and 13C NMR data.