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Schiff bases formed from the condensation reaction of S-benzyldithiocarbazate (SBDTC) and S- methyldithiocarbazate (SMDTC) with selected diketones containing isatin derivatives namely isatin,5- fluroisatin,5-chloroisatin,5-bromoisatin and methylisatin have been synthesised.Complexes of cobalt (II), nickel (II), copper (II), zinc (II) and cadmium (II) with these Schiff bases were prepared.X-ray crystallographic study of SB5ClISA and SB5BrISA Schiff bases proved that the condensation reaction between SBDTC with the isatin derivatives occur at the carbonyl position number 3 in the isatin ring.Crystal structure analyses of Co (II) and Ni(II) complexes are six-coordinate with a distorted octahedral geometry.Crystal structure of the Cu(II) complex exhibited distorted square planar geometry. The Schiff bases and their metal complexes were evaluated for cytotoxic and antimicrobial activity. Cytotoxic screening was carried out against MCF-7 and MDA-MB-231 human breast cancer cells. Some of the compounds were found very active with a CD50 values lower than Tamoxifen. All compounds were found to have low or no activity against the selected bacteria and fungal strains.