Antioxidants are known to prevent oxidative stress-induced damage to the biomolecules and thus, delay the onset of cancers and many age-related diseases. Therefore, the development of novel and potent antioxidants is justified.During this study, we synthesized symmetrical Bis-Schiff bases of carbohydrazide 1-27, and evaluated their in vitro antioxidative activity and cytotoxic activity.Among synthesized compounds, six compounds 20 (IC50 = 12.89 ± 0.02 μM), 16 (IC50 = 14.32 ± 0.43 μM), 17 (IC50 = 18.52 ± 0.83 μM), 19 (IC50 = 22.84 ± 0.62 μM), 24 (IC50 = 35.1 ± 0.82 μM) and 15 (IC50 = 40.03 ± 1.06 μM) showed an excellent 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, better than the standard butylatedhydroxyanisole (BHA) (IC50 = 44.6 ± 0.6 μM). Likewise, two compounds 16 (IC50 = 4.3 ± 1.3 μM) and 20 (IC50 = 6.6 ± 1.6 μM) showed oxidative burst scavenging activity better than the standard drug ibuprofen (IC50 = 11.2 ± 1.9 μM). Some synthesized compounds showed good to moderate toxicity against prostate cancer (PC-3) cell lines.This study has identified potent antioxidants and good cytotoxic agents with the potential to further investigate.