Synthesis of N-(1-nitropyren-6-yl and 8-yl)-2'-deoxyribonucleosides

Article abstract of DOI:10.1021/tx00047a009

A new type of 1-nitropyrene-DNA adduct via addition-elimination reaction was synthesized. Treatment of fluorinated 1-nitropyrene with 3'- and 5'-O- protected 2'-deoxyribonucleoside in dimethyl sulfoxide at 140 °C afforded N- (1-nitropyren-6-yl or 8-yl)-2'-deoxyribonucleoside. These DNA adducts resulted from addition of the exocyclic amino group of deoxynucleosides to the fluorinated carbon of the fluoro-1-nitropyrene following elimination of fluoride anion. This is the first report that describes the 1-nitropyrene- DNA adducts in which aromatic ring moiety of 1-nitropyrene is covalently linked to the exocyclic amino group of the deoxyribonucleoside. From our findings, we suggest that the addition-elimination reaction may be responsible for the formation mechanism of the putative 1-nitropyrene-DNA adducts in vivo.