A series of novel quinoxaline based bisspirooxindolo-pyrrolizidines were synthesized through 1,3-dipolar cycloaddition under ultrasonication with shorter reaction time and good yields. The compounds were well characterized by various spectroscopic methods and finally single crystal X-ray diffraction method (4c, 4d). DFT energy calculations confirm the regioselectivity due to enone umpolung effect. The in vitro anti-cancer activity of the synthesized compounds (4a-s) shows that the compounds 4g and 4q exhibited good anti-cancer activity with IC50 values14.51 +/- 1.1 and 11.36 +/- 0.23 mu M against DU-145 prostate cancer cell line; and 16.78 +/- 0.95 and 14.28 +/- 0.64 mu M against Hela cervical cancer cell lines when compared to the standard anti-cancer drug doxorubicin (1.75 +/- 0.06 and 1.35 +/- 0.09 mu M). In silico molecular docking studies indicated that the synthesized compounds may serve as a potential lead for the further development of novel anti-cancer agents.

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