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Paper | Regular issue | Vol 29, No. 6, 1989, pp.1127-1135
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4905
Isolation, Structure Elucidation, and Synthesis of the Major Anaerobic Bacterial Metabolite of the Dietary Carcinogen 2-Amino-3,4-dimethyl-3H-imidazo[4,5-f]quinoline (MeIQ)

Mohammad Bashir, David G. I. Kingston,* Robert J. Carmen, Roger L. Van Tassell, and Tracy D. Wilkins*

*Department of Chemisry, Virginia Polytecnic Institute and State University, Blacksburg, Virginia 24061-0212, U.S.A.

Abstract

Incubation of the heterocyclic cooked food mutagen 2-amino-3,4-dimethyl-3H-imidazo[4,5-f]quinoline (MeIQ, 3) with mixed human fecal microflora under anaerobic conditions yielded 2-amino-3,6-dihydro-3,4-dimethyl-7H-imidazo[4,5-f]quinolin-7-one (HOMeIQ, 4) as the major detectable metabolite. HOMeIQ (4) was synthesized in six steps from 6-bromo-7-methylquinoline (5).