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

✍ Scribed by Swarna A. Gamage; Julie A. Spicer; Gordon W. Rewcastle; William A. Denny

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 201 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(96)02396-9

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✦ Synopsis

A new synthesis of substituted acridine-4-carboxylic acids 2 from methyl 2-[N-(2-earboxyphenyl)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-earboxylates (8), followed by base hydrolysis. Direct amidation of 8a provides a new route to the clinical anticaneer drug DACA (3) which avoids use of the irritant acid 2a.

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