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Paper | Regular issue | Vol 32, No. 10, 1991, pp.1933-1945
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5808
Synthesis of 11-Aminosubstituted 6,8-Dimethyl-12H-[1]benzo[5,6]thiopyrano[2,3-c]quinolin-12-ones as Benzo Analogues of Lucanthone

Martine Croisy-Delcey,* Christiane Huel, Alain Croisy, and Emile Bisagni

*URA 1387 CNRS, Section de Biologie Bâtiments 110-112, Institut Curie, 15 Rue Georges Clémenceau 91405 Orsay, France

Abstract

Condensation of acetonyl 2-methyl-5-chlorophenyl sulfide with potassium isatates led to 2-methyl-3-(2-methyl-5-chlorophenylthio)-4-quinolinecarboxylic acids. Polyphosphoric acid cyclodehydration then afforded 6,8-dimethyl-11-chloro-12H-[1]benzo[5,6]thiopyrano[2,3-c]quinolin-12-ones whose substitution by dialkylaminoalkylamines gave the title compounds. Whereas 2- and 3-methoxy-substituted products were transformed into their phenolic derivatives by hydrobromic acid. Regioselective oxidation of the 6-methyl group successively led to 6-formyl, 6-carboxy and 6-H- series. Evaluation of cytotoxic and antitumor properties showed that these new benzolucanthone analogues are devoid of biological activity.