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Objective: The present study was aimed to determine cytotoxic and apoptotic activity of isatin semicarbazones against mammary carcinoma. Methodology: The preparation of these target compounds involved substitution at the third position of the isatin nucleus along with chemical modification at the nitrogen atom of the scaffold to obtain more potent derivatives. The synthesized analogs were characterized by recording their melting point and R f values along with IR, NMR and mass spectra. An antioxidant study and Cytotoxic Studies were performed by DPPH, Nitric oxide scavenging method and MTT assay methods. Results: The results revealed that all the test compounds (5a-5d) exhibited good anti oxidant activity. The synthesized compounds were then screened for in-vitro cytotoxicity by MTT cell proliferation assay method against breast cancer cell lines including MCF-7 and BT-549 with derivative 5a exhibiting maximum activity in both the cell lines. DNA fragmentation studies further indicated that 5a was involved in apoptotic process. Conclusion: Interestingly, it was observed that while all the synthesized compounds seemed active, 5a exhibited a superior ability to induce apoptosis.