Synthesis of the N2-deoxyguanosine adduct of the potent dietary mutagen IQ.
[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.
Stover
James S
JS
Department of Chemistry, Center in Molecular Toxicology, and Vanderbilt Institute of Chemical Biology, Vanderbilt University, VU Station B 351822, Nashville, Tennessee 37235-1822, USA.
Rizzo
Carmelo J
CJ
D000478:Alkylation; D002384:Catalysis; D003849:Deoxyguanosine / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry*
D011804:Quinolines; C029216:2-amino-3-methylimidazo(4,5-f)quinoline; D010165:Palladium; D003849:Deoxyguanosine