The synthesis of Schiff base transition metal complexes always appears to be fascinating because of the possibility of obtaining coordination compounds of unusual structure and stability. These compounds possess special attention in the field of pharmaceuticals because of their wide spectrum of biological applications. Schiff base complexes form versatile compounds which actively take part in metalloenzymes and also can act as biomimetic models because of their closeness to natural proteins and enzymes. Hence, the present paper mainly aims in the synthesis of Schiff base ligand by modifying the functional group of the drug, diclofenac and using that Schiff base ligand four novel metal complexes of Cu(II), Co(II), Ni(II), and Zn(II) were prepared. The nature of bonding and the stereochemistry of the metal complexes can be deduced from elemental analyses, molar conductance, magnetic susceptibility, IR, electronic, 1 H NMR and Mass. The analytical data reveals that the metal to ligand ratio is 1:2. Due to lower molar conductivity values, the metal complexes are considered nonelectrolytes. The spectral analysis data describes that all the metal complexes possess octahedral geometry. The drug diclofenac synthesized Schiff base ligand and novel metal complexes were subjected to antimicrobial as well as anti-inflammatory activities. The Schiff base ligand and metal complexes show promising biological activities.