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

Authors
Mallesha, H Kumar, KRR Rangappa, KS
Citation
H. Mallesha et al., 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, SYNTHESIS-S, (16), 2001, pp. 2415-2418
Citations number
49
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
16
Year of publication
2001
Pages
2415 - 2418
Database
ISI
SICI code
0039-7881(200112):16<2415:SONAUC>2.0.ZU;2-7
Abstract
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 achi eved in a lead tetraacetate (LTA) oxidation reaction. Compound 9 reacts wit h deoxyguanosine (dG) at pH 7.0 to give N-(benzoyl)-N-(deoxyguanosin-8-yl)- 2-aminofluorene (10). Subsequent debenzoylation with the heterogeneous syst em (sodium carbonate/methanol) leads to the C8-adduct, N-(2'-deoxyguanosin- 8-yl)-2-aminofluorene (11).