The new dibasic tetra dentate (ONNO) Schiff base ligands (L1and L2) were synthesized by the reaction of terephthalaldehyde with 2-amino 4-chlorophenol and X (where, X=2-amino 4-methylphenol, 2-aminophenol) in 1:1:1 molar ratio. The macrocyclic binuclear Co (II), Ni (II) and Cu ((II) metal complexes were prepared in ligand to metal ratio 2:2. The elements, metal structure and binding sites of Schiff bases and its complexes were established by diverse studies like Elemental, Molar conductance, UV, Magnetic moment, FT-IR, H1 and C13 NMR, ESI-Mass, ESR, Thermal and Powder-XRD. The above spectral studies reveal that the ligands are a tetra dentate and its metal complexes possess a square planar geometry. All the compounds were screened for antibacterial, antioxidant and DNA cleavage and the results show high activity for metal complexes than the ligand. The DNA binding studies of Cu(II) complexes were measured by electronic absorption method. In vitro cytotoxicity assay of Cu (II) complexes were tested for their tumour inhibiting potential against MCF-7 human breast cancer cell by using MTT method.