The rearrangement of a new alpha -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).

This study demonstrates a novel method for synthesis of N-acetoxy-N-benzoyl-2-aminofluorene, an ultimate carcinogen, using lead tetraacetate oxidation of alpha-phenyl-N-(2-aminofluoreny

Synthesis

Synthesis of N-acetoxy-N-benzoyl-2-aminofluorene, an ultimate carcinogen by LTA oxidation of alpha-phenyl-N-(2-aminofluorenyl)nitrone, and N-(2 `-deoxyguanosin-8-yl)-2-aminofluorene

Paper

Synthesis of N-acetoxy-N-benzoyl-2-aminofluorene, an ultimate carcinogen by LTA oxidation of alpha-phenyl-N-(2-aminofluorenyl)nitrone, and N-(2 `-deoxyguanosin-8-yl)-2-aminofluorene

References

Citations