Heterocyclic quinones VIII. Synthesis and anti-neoplastic evaluation of 7-substituted-1H-pyrroloquinoline-6,9-diones and 3-substituted-11H-indoloquinoline-1,4-diones

Article abstract of DOI:10.1016/0223-5234(87)90264-9

7-Methoxy-2,3,4-trimethyl-1H-pyrrolo<3,2-c>quinoline-6,9-dione 13 and 3-methoxy-6-methyl-11H-indolo<3,2-c>quinoline-1,4-diones 15 and 19 were obtained by oxidation of quinolinamines 9, 11 and 12 with Fremy's salt.The synthesis method of amines 9 and 11 consists of creating the pyrrole or indole nucleus according to Fischer's indolic reaction applied to hydrazones 8 and 10.Aromatization of 11 yielded quinolinamine 12.The nucleophilic substitution of methoxy by aziridine leads to quinones 14, 16 and 20.These quinones are highly cytotoxic for L1210 cells, but no activity could be established for the P388 lymphocytic leukemia in vivo.Keywords: anti-tumor agents / cytotoxicity / Fischer indolic reaction / Fremy's salt / heterocyclic quinones / 11H-indolo<3,2-c>quinoline-1,4-diones / 1H-pyrrolo<3,2-c>quinoline-6,9-diones / P388 lymphocytic leukemia