Synthesis and evaluation of quindoline and its analogue as potential anticancer agents

Abstract

Several derivatives of quindoline, 10H-(indolo[3,2-b]quinoline), alkaloids were prepared by the modification of the Pfitzinger quinoline reaction. The conversion of quindoline was 71% while that of another compound, 2,10-bis(dimethylaminoethyl)-indolo[3,2-b]quinoline, was 64%. In the evaluation of the cytotoxicities of the two compounds using five human ovarian cancer cell lines, namely SKOV-3, A2780, A2780R, CHI, and CHIR, quindoline gave minimum inhibitory concentration (IC50) results of 66, 21.5, 24.5, 15.5, and 30 M, respectively whiles the more potent compound, 2,10-bis(dimethylaminoethyl)-indolo[3,2-b]quinoline, gave 6.3, 12.5, 10.5, 8.4, and 12.5 M, respectively. A third compound, 2-(3-hydroxypropan-1-yl)-10H-indolo[3,2- b]quinoline, was prepared by the Heck reaction in a yield of 70%