79953-08-5

Usage

General Description

2-amino-8-(4-methylphenyl)-3,7-dihydro-6H-purin-6-one is a chemical compound with the molecular formula C13H12N4O. It is a derivative of purine and is a member of the xanthine family of compounds. This chemical is a potent adenosine receptor antagonist and is commonly used in research as a tool to study the role of adenosine receptors in various biological processes such as sleep, inflammation, and cardiovascular function. It has also been investigated for its potential therapeutic applications in conditions such as Parkinson's disease and cancer. The compound is a white solid that is sparingly soluble in water and stable under normal conditions.

Upstream product

• 79953-04-1 2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-p-tolyl-1,9-dihydro-purin-6-one 

Relevant academic research and scientific papers

Concerning the hydrolytic stability of 8-aryl-2′-deoxyguanosine nucleoside adducts: Implications for abasic site formation at physiological pH

(Chemical Equation Presented) Direct addition of aryl radical species to the C8-site of 2′-deoxyguanosine (dG) affords C 8-aryl-dG adducts that are produced by carcinogenic arylhydrazines, polycyclic aromatic hydrocarbons (PAHs), and

Reactions of Benzenediazonium Ions with Guanine and Its Derivatives

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.