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A simple and efficient BF₃-OEt₂ promoted C3-alkylation of indole has been developed to obtain3-indolylsuccinimidesfrom commercially available indoles and maleimides, with excellent yields under mild reaction conditions. Furthermore, anti-proliferative activity of these conjugates was evaluated against HT-29 (Colorectal), Hepg2 (Liver) and A549 (Lung) human cancer cell lines. One of the compounds, <b>3w</b>, having <i>N</i>,<i>N</i>-Dimethylatedindolylsuccinimide is a potent congener amongst the series with IC₅₀ value 0.02 µM and 0.8 µM against HT-29 and Hepg2 cell lines, respectively, and compound <b>3i</b> was most active amongst the series with IC₅₀ value 1.5 µM against A549 cells. Molecular docking study and mechanism of reaction have briefly beendiscussed. This method is better than previous reports in view of yield and substrate scope including electron deficient indoles.