Two molybdenum complexes, MoHL1 and MoHL2, are prepared from the corresponding tetradentate salen type (ONNO) ligands, HL1 and HL2, obtained from 3, 5‐dichloro salicylaldehyde, and substituted o‐phenylenediamines. The complexes are characterized by 1H NMR, FTIR, HRMS, and UV‐visible spectral techniques. The DFT studies provide insight into their structural parameters. The band gap energy and molecular orbital energies influence the charge transfer interactions within the molecule. Further, the complexes are assessed for their antioxidant efficacy, α–amylase inhibitory potential, binding propensity with deoxyribonucleic acid, and cytotoxicity studies against breast cancer cell line, MCF7. The DPPH assay demonstrates high radical scavenging ability, as evidenced by the IC50 value of 133.85±1.18 μg/mL, higher than ascorbic acid. From the results of α–amylase inhibitory assay, MoHL1 shows good inhibitory action with the IC50 value of 32.72±2.49 μg/mL higher than that of the standard acarbose. The absorption titration method, to track the binding interactions of the metal complexes with DNA, shows a marked hyperchromic effect indicating preferential binding of the complexes to the grooves of DNA helical structure. MoHL2 exerts higher cytotoxicity against cancer cell lines than MoHL1. Thus, the complexes have the potential to be developed as antidiabetic and anticancer agents.