A protocol for the synthesis of 3-((2-mercaptoquinolin-3-yl)methyleneamino)-5-bromobenzofuran-2-carboxamide has been developed by the condensation of 3-amino-5-bromobenzofuran-2-carboxamide with 3-formyl-2- mercaptoquinoline. Metal complexes of the Schiff base were prepared from their chloride salts of Co(II), Ni(II), Cu(II), Cd(II), Zn(II) and Hg(II) in ethanol. The prepared Schiff bases and chelates have been characterized by elemental analysis, molar conductance, magnetic susceptibilities, FTIR, 1HNMR, electronic spectral studies, ESR and mass. The molar conductance studies show non-electrolytic behavior of the complexes. The ligands and their metal complexes has been screened for their antibacterial and antifungal activities and its activity increases on complexation.