Abstract
4-Chloro-8-methoxy-11H-indolo[3, 2-c]quinoline could be obtained from 8-chloro-2, 3-dihydro-1H-quinolin-4-one and 4-methoxyphenylhydrazine by applying Fischer's indole synthesis. Its nitration led to the 7-nitro derivative which was reduced to 7-amino-4-chloro-8-methoxy-11H-indolo[3, 2-c]quinoline when Raney nickel was employed as a catalyst and to 7-amino-8-methoxy-11H-indolo[3, 2-c]quinoline when palladium charcoal was used. Oxidation of the amines by potassium nitrosodisulfonate produced the corresponding 11H-indolo[3, 2-c]quinoline-7, 10-diones. Diplacement of the methoxy group by (N, N-diethylamino)ehylamine or by N-methylpiperazine afforded the 8-aminoquinones. The quinones unsubstituted at the 4-position were more cytotoxic than the previously described 2-methoxy-11H-indolo[3, 2-c]-quinoline-1, 4-diones.
