Reactions of esters of N-hydroxy-2-acetamidophenanthrene with cellular nucleophiles and the formation of free radicals upon decomposition of N-acetoxy-N-arylacetamides.

The sulfate ester of 7V-hydroxy-2-acetamidophenanthrene was prepared and was found to react significantly with methionine, adenosine, and guanosine. The adduci from the methionine reaction was characterized as 1-methylmercapto-2acetamidophenanthrene. The levels of reaction with adenosine and guanosine were comparable, in contrast with the observation that TV-acetoxy-2-acetamidofluorene shows a marked preference for guanosine as a substrate among the nucleosides. Although the level of reaction was lower, 7V-acetoxy-2-acetamidophenanthrene also reacted equally well with adenosine and guanosine. Molecular orbital calculations suggested that the previously studied adduct-forming abilities of jV-acetoxy-TV-arylacetamides might be related to their ability to form radical cations. On this basis, the abilities of these compounds to decolorize the stable free radical 2,2-diphenyl1-picrylhydrazyl were tested. jV-Acetoxy-2-acetamidofluorene rapidly decolorized 2,2-diphenyl-l-picrylhydrazyl in 20% ethanol at 45°, 7V-acetoxy-2-acetamidophenanthrene acted