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New series of oxindol-based heterocyclic entities (2–11) have been designed and synthesized using indolin-2-one derivatives as key materials (1a–d). The chemical structures of the new synthesized compounds were characterized by FTIR, 1HNMR, 13CNMR, MS spectroscopy and elemental analyses. Three of the newly synthesized compounds were tested for anticancer activity in the National Cancer Institute (NCI) against human panel breast cancer cell line MCF7, from the in vitro assays compound 6c presented promising anti-cancer activity using Doxorubicin as a reference. Compound 6c could be a lead compound for discovery of new anticancer agent.