A novel series of transition metal complexes of Co(II), Ni(II), Cu(II) and Zn(II) have been synthesized from their corresponding metal chlorides and macrocyclic Schiff base ligand derived from, 4-aminoantipyrine, 2,3-butadion and O-Phenylenediamine. Several tools like elemental analyses, magnetic susceptibility, molar conductance, Mass, FT-IR, Far IR, UV-Vis, VSM, 1H NMR, 13C NMR, SEM, EDX and ESR have been used to obtain the chemical structures of synthesized transition metal complexes. The UV-Vis, magnetic susceptibility and ESR the spectral data reveal that all complexes are found to have octahedral geometry. The antimicrobial screening test indicates that the metal complexes of Cu(II) have good antimicrobial activity than other metal complexes. DNA cleavage studies show the effectiveness cleavage of all the complexes.