A series of Zn(II) and Co(II) complexes have been synthesized by template condensation of bis(benzil)-4-chloro-1,2-phenylenediamine and bis(benzil)-4-fluoro-1,2-phenylenediamine, respectively, with 4-chloro-1,2-phenylenediamine and 4-fluoro-1,2-phenylenediamine in the presence of transition metal chlorides. The complexes have been characterized by physicochemical and spectroscopic techniques. Based on these studies, an octahedral geometry has been proposed around the metal ions. The newly synthesized ligands and their metal complexes have been screened for antimicrobial and anticancer activities. The in vitro cytotoxicity towards the HeLa cell line has been evaluated by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay.