The new imine  ligands were synthesized by the condensation reaction between 2-hydroxynaphthaldehyde or 3-ethoxysalicylaldehyde and o-phenylenediamine s in 1:1 molar ratio. The ligands react with vanadyl  acetylacetonate  in 1:1 molar ratio to give distorted and square pyramidal geometry for tri- and tetra-dentate imine complexes, respectively. All the complexes are non– hygroscopic in nature and stable to the atmosphere. The synthesized ligands and the isolated imine complexes have been characterized by elemental analysis, thermal analysis,  molar conductivity, IR, electronic spectroscopy, magnetic moment measurements. The results obtained from these studies and their interpretation used to solve the structure of the complexes. Moreover, the prepared compounds  have been subjected to antimicrobial activity against different types of bacteria and fungi. The results indicate the enhanced activity of metal complexes over their parent ligands. Moreover,  DNA binding of the prepared complexes  were performed using  electronic absorption spectra, viscosity and gel electrophoresis measurements. Furthermore, anticancer activity of the prepared compounds were tested against Hepatocellular carcinoma and  colon carcinoma  cells and the results showed enhancement in the activity from ligand to complex.