A series of new 6-[(N1-aryl-1H-1,2,3-triazol-4-yl)methyl]-6H-indolo[2,3-b]quinoxaline derivatives 7ai–ix and 7bi–vi is synthesized by a simple multi-step protocol starting from isatin 1a or 5-fluoroisatin 1b. These compounds are screened against lung (A-549), cervical (HeLa), and prostate (DU-145) human cancer cell lines to evaluate their cytotoxic effect. Of all the compounds tested, five compounds showed moderate cytotoxicity against human reproductive organ cell lines, while others exhibited lower cytotoxicity against different human cancer cell lines. An elegant synthesis of these complex molecules and their cytotoxicity data are presented.