In the present investigation, a series of newly reported Schiff bases of nitrogen containing heterocyclic nucleus evaluated for their possible Cytotoxic and Antioxidant activities. The synthesised compounds 4,4'-(4phenylpyridine-2,6-diyl)bis (N-benzylideneaniline) derivatives (6a-o) were synthesized from an efficient condensation reaction of 4-Substituted Phenyl-2, 6-bis(4-Amino Phenyl) Pyridine, with Substituted Aromatic Aldehydes. The characterisation of the newly synthesized compounds have been confirmed from its elemental analysis and spectral studies (IR, 1 HNMR, 13 CNMR and Mass). The synthesized Schiff bases were evaluated for their cytotoxic activity and Antioxidant activity by MTT assay and Nitric oxide (NO) radical scavenging method respectively.