A new Schiff base 6,8,15,17-tetramethyl-7,16-dihydrodibenzo-1,4,8,11-tetraazacyclotetradecine was synthesized by condensation of 1,2-diaminobenzene and pentane-2,4-dione in an alcoholic medium. The synthesized Schiff base and its metal complexes were characterized by micro elemental analysis, magnetic susceptibility, molar conductivity, IR, UV-Vis and NMR spectral data. On the basis of spectroscopic data suggest an octahedral geometry for the Ni(II) complex and a distorted octahedral geometry for the Cu(II) complex. DFT studies at the def2-SVP level show that the HOMO-LUMO energy gap decreases from 4.70 eV (ligand) to 3.80 eV in Cu-complex, indicating enhanced reactivity. Molecular docking with p53 anti-tumor protein DNA revealed a strong intercalation mode at the major groove of DNA.