Metallation of new imines 2-(4-(Dimethylamino)benzylidene- amino)benzenethiol (1) and 2-(4-nitrobenzylideneamino)-benz- enethiol(5) with Hg(II), Ni(II) acetate, and palladium chloride afforded metallated products (2), (3), and (4) in the form of monomercurated, dinickel nickel bis-, monopalladated products and monometallated products of Hg++ and Ni++ (6) and (7), and monopalladated cyclized product (8), respectively. Compounds (1) and (5) were prepared from the reaction of o-aminothiophenol with N,N-dimethylaminobenzaldehyde and p-nitrobenzaldehyde in ethyl alcohol. Elemental analyses, IR, 1HNMR, and mass spectral elucidated the structures. All the newly synthesized compounds have been evaluated for their antimicrobial activity against gram positive and gram negative bacteria and fungi. Compounds (4) and (8) exhibited in vitro anticancer activity toward breast cancer.