Synthesis and evaluation of quindoline and its analogue as potential anticancer agents
Chemistry of Natural Compounds
Department of Chemistry, University of Cape Coast, Cape Coast, Ghana; Chemistry Department, University of Reading, Reading RG6 7AD, United Kingdom; School of Chemistry, Queen's University of Belfast, Belfast BT 9 5AG, United Kingdom
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%. © 2014 Springer Science+Business Media New York.