Some new complexes derived from VO(II), Ag(I) and Pd(II) metal ions and HNA imine ligand (L) i.e. (2-[(6-Allylidene-2-hydroxy-cyclohexa-1,3-dienylmethylene)-amino]-benzoic acid) have been prepared and their structures are elucidated via molar conductance, elemental analyses, IR, NMR, magnetic susceptibility estimations and electronic spectral studies. Moreover, stability constants of the synthesized complexes were evaluated utilizing spectrophotometric technique. On the basis of molar conductance and elemental analyses the metal imine chelates had been found to have structure [M(L)], where M = Pd(II), VO(II) and Ag(I),L=ligand. The results indicate that the prepared HNA imine ligand acts as tri-dentate moiety via nitrogen atom of azomethine group and two oxygen atoms of phenolic and carboxylic groups. All the complexes were found to be monomeric 1: 1 (M:L) stoichiometry in nature with square planner geometry for Pd(II), tetrahedral geometry for Ag(I), and distorted square pyramidal for VO(II). The theoretical DFT calculations were applied to verify the molecular geometry of chelators and their metal chelates. The geometry optimization results are in agreement with experimental observations. The prepared HNA imine ligand and its metal chelates were checked towards numerous sorts of plant pathogenic fungi and bacteria to evaluate their antimicrobial properties. The results of these studies indicate that the metal complexes exhibit a stronger antibacterial and antifungal efficiency compared to their corresponding imine ligand In addition, the interaction of the metal imine chelates via CT-DNA had been observed by way of utilization viscosity, gel electrophoreses and spectral studies estimations. The absorption titration studies revealed that each of these complexes is an avid binder to calf thymus-DNA. Also, there were appreciable changes in the relative viscosity of DNA, which is consistent with enhanced hydrophobic interaction of the aromatic rings and intercalation mode of binding. Additionally, the cytotoxic activity of the investigated compounds on various cancer cell lines and shown promising results which had been made them prospective compounds of avail in antibiotic and anticancer medicament studies. Furthermore, the docking studies of the prepared compounds were reported for confirming biological results.