The Schiff base ligand, (E-N-((E)-3-phenylallylidene) aniline was prepared by from cinnamaldehyde with aniline via green route synthetic method. Reactions of the ligand with Mn(II) and Cu(II) precursors generate new complexes. The structures of the ligand and the new metal complexes were elucidated using various physicochemical measurements (FT-IR, NMR, Mass, UV-Vis, and elemental analyses). Further, the in vitro antibacterial and antifungal studies divulge that the Cu(II) complex exhibited potent activity over the ligand and Mn complex. In contrast the new manganese complex outperformed the nickel complex as well as the ligand in the cleavage of PUC57 DNA by the involvement of free radicals. Furthermore the in vitro cytotoxicity of the compounds against oral cancer cell line has been examined. The molecular docking studies revealed that the Mn(II) complex interact with SER-15 through hydrogen bonding and it is closely associated with Bax protein with three hydrogen bond interactions through the amino acids residues GLN-32 and ASP-33. Ultimately, the most frequently used parameters for the prediction of drug-likeness were calculated for the new Schiff base compounds.