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1. ChemInform Abstract: A New Synthesis of Substituted Acridine-4-carboxylic Acids and the Anticancer Drug N-(2-(Dimethylamino)ethyl)acridine-4-carboxamide (DACA)

Author

Gordon W. Rewcastle, William A. Denny, Julie Ann Spicer, and Swarna A. Gamage

Subjects
chemistry.chemical_compound, Hydrolysis, Chemistry, Acridine, Acridine derivatives, Trifluoroacetic acid, N-(2'-(dimethylamino)ethyl)acridine-4-carboxamide, General Medicine, Medicinal chemistry, Anticancer drug, Benzoates
Abstract

A new synthesis of substituted acridine-4-carboxylic acids 2 from methyl 2-[ N -(2-carboxyphenyl)amino]benzoates ( 4 ) is reported, via NaBH 4 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 DACA ( 3 ) which avoids use of the irritant acid 2a .

Published
2010
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