Synthesis of O-Acetyl-N (4-biphenylyl)hydroxylamine (“N[BOND]Acetoxy-4-aminobiphenyl”), an Ultimate Metabolite of Carcinogenic 4-Aminobiphenyl, and Its Reaction with Deoxyguanosine


  • This work was supported by the Fonds der Chemischen Industrie, by the Deutsche Forschungsgemeinschaft, and by BASF AG.


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The carcinogenicity of aromatic amines has been known since 1895. It has now been possible for the first time to convert the hydroxylamine derivative generated from 4-aminobiphenyl 1 into the crystalline title compound 2 in vitro. 2 reacts with deoxyguanosine to give the same “adducts” which, e.g., are also obtained when 1 is administered to dogs and the DNA is subsequently cleaved enzymatically (Aryl = 4-biphenylyl).