Tetrahedron letters

A new synthesis of substituted acridine-4-carboxylic acids and the anticancer drug N-[2-(dimethylamino) ethyl] acridine-4-carboxamide (DACA)

SA Gamage, JA Spicer, GW Rewcastle, WA Denny

Index: Gamage, Swarna A.; Spicer, Julie A.; Rewcastle, Gordon W.; Denny, William A. Tetrahedron Letters, 1997 , vol. 38, # 4 p. 699 - 702

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Citation Number: 19

Abstract

A new synthesis of substituted acridine-4-carboxylic acids 2 from methyl 2-[N-(2- carboxyphenyl) amino] benzoates (4) is reported, via NaBH4 reduction of the corresponding imidazolides (5), oxidation of the resulting alcohols 6 to aldehydes 7, and cyclisation of these with trifluoroacetic acid to the methyl acridine-4-carboxylates (8), followed by base hydrolysis. Direct amidation of 8a provides a new route to the clinical anticancer drug ...