Synthesis of N-Acetoxy-N-benzoyl-2-aminofluorene, an Ultimate Carcinogen by LTA Oxidation of α-Phenyl-N-(2-aminofluorenyl)nitrone, and N-(2′-Deoxyguanosin-8-yl)-2-aminofluorene

Abstract

The rearrangement of a new α-phenyl-N-(2-aminofluorenyl)nitrone (8) to a new ultimate carcinogen, N-acetoxy-N-benzoyl-2-aminofluorene (9) is achieved in a lead tetraacetate (LTA) oxidation reaction. Compound 9 reacts with deoxyguanosine (dG) at pH 7.0 to give N-(benzoyl)-N-(deoxyguanosin-8-yl)-2-aminofluorene (10). Subsequent debenzoylation with the heterogeneous system (sodium carbonate/methanol) leads to the C8-adduct, N-(2′-deoxyguanosin-8-yl)-2-aminofluorene (11).

N-acetoxy compound - LTA oxidation - α-phenyl-N-(2-aminofluorene)nitrone - dG adduct, N-(2′-deoxyguanosin-8-yl)-2-aminofluorene

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