Synthesis of the N2-deoxyguanosine adduct of the potent dietary mutagen IQ.

Org Lett

Department of Chemistry, Center in Molecular Toxicology, and Vanderbilt Institute of Chemical Biology, Vanderbilt University, VU Station B 351822, Nashville, Tennessee 37235-1822, USA.

Published: December 2004

[structure: see text] After bioactivation, the potent dietary mutagen 2-amino-3-methylimidazo[4,5-f]-quinoline (IQ) reacts with DNA to give two regioisomeric adducts of deoxyguanosine. The synthesis of the minor N2-adduct has been achieved utilizing the Buchwald-Hartwig palladium-catalyzed N-arylation reaction as the key step.

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http://dx.doi.org/10.1021/ol047851mDOI Listing

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