79953-01-8Relevant academic research and scientific papers
Different Patterns of Mutagenicity of Arenediazonium Ions in V79 Cells and Salmonella typhimurium TA102: Evidence for Different Mechanisms of Action
Lawson, Terence,Gannett, Peter M.,Yau, Wai-Ming,Dalal, Nar S.,Toth, Bela
, p. 2627 - 2635 (2007/10/03)
The edible mushroom Agaricus bisporus contains several arylhydrazines and arenediazonium ions that are genotoxins.The mechanism whereby arylhydrazines and arenediazonium ions are genotoxic is unknown and may be due to the arenediazonium ion itself or to a
Reactions of Benzenediazonium Ions with Guanine and Its Derivatives
Hung, Ming-Hong,Stock, Leon M.
, p. 448 - 453 (2007/10/02)
Guanine reacts with several benzenediazonium ions rapidly in aqueous solution at pH 10.5 to form 8-(arylazo)guanines in good yield.The reaction of guanine with 4-bromobenzenediazonium ion forms ε-guanine about 50-fold more rapidly than the reaction of adenine with this ion to yield 6-purine under these experimental conditions.Guanosine reacts much more slowly than guanine with the benzenediazonium ions in aqueous solution at pH 8.5 or 10.5 to give 8-arylguanosines.The structures of these products were established by their spectroscopic properties and by their quantitative conversion to 8-arylguanines. 5'-Guanylic acid also reacts quite slowly with the benzenediazonium ions in aqueous solution at pH 10.5.Only the compounds with strong electron-withdrawing groups yield N-2 triazenes at ambient temperature.No 8-aryl or 8-arylazo compounds are formed with 5'-guanylic acid at this temperature.However, 4-bromo- and 4-sulfobenzenediazonium ions react with 5'-guanylic acid at higher temperatures to yield the 8-aryl-5'-guanylic acids in low yield.The structures of these products were proven by hydrolysis to 8-arylguanines.The 8-arylguanosines and the 8-aryl-5'-guanylic acids are formed via free-radical phenylation reactions.The factors governing the reactivity of the adenines and the guanines are discussed.
