Schiff bases are considered as privileged ligand in coordination chemistry as they easily form stable complexes with most transition metal complexes. In this paper, a novel Schiff base ligand derived from Thiophene-2-carboxaldehyde (TPC) and 4,4’ diamino diphenyl methane (DDM) and its transition metal complexes Cu(II), Zn(II), Co(II) and Ni(II). Antimicrobial, antioxidant, anti-inflammatory, larvicidal, DNA cleavage activity against standard at variable concentrations revealed that the Cu(II), Zn(II), Co(II) and Ni(II) complexes show enhanced antimicrobial, free radical scavenging and anti-inflammatory activities as compared to TPC and DDM.