SYNTHESIS OF 11-AMINOSUBSTITUTED 6,8-DIMETHYL-12H-[1]-BENZO[5,6]THIOPYRANO[2,3-C]QUINOLIN-12-ONES AS BENZO ANALOGS OF LUCANTHONE

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.