A new series of transition metal complexes of Schiff base ligand containing 4-hydroxy-3-methoxybenzaldehyde (vanillin), 4-aminoantipyrine and 2-aminothiazole have been synthesized. All the complexes have been characterized by the use of elemental analyses, molar conductance values, magnetic moments, FT-IR, H-NMR, Mass and electronic absorption data. The Schiff base is found to act as tridentate ligand leading to an octahedral geometry of the complexes. The ESR spectra of copper complex in Tetracyanoethylene (TCNE) solution were recorded at room temperature (RT) and liquid nitrogen temperature (LNT) and its significant features are reported. The redox behavior of the copper complex at RT was well studied. The in silico DNA results revealed that cobalt and copper complexes are bound to the “Minor groove” and nickel and zinc complexes are bound to the “Major groove” portion of DNA through hydrogen bonds and hence they are called “Minor groove and Major groove binders” respectively. The Schiff base and its metal complexes have been screened for their in vitro antibacterial activities.