21149-25-7

Usage

Uses

Used in Pharmaceutical Industry:
Adenine-7-oxide is used as a potential therapeutic agent for its antioxidant properties and ability to protect cells from oxidative stress. It may contribute to the development of new drugs for the treatment of various diseases.
Used in Research Applications:
Adenine-7-oxide is used as a research tool to study its biological functions and potential uses in understanding the mechanisms of cell signaling, energy storage, and metabolism. Further research is needed to explore its full potential in the development of new therapeutic strategies.

InChI:InChI=1/C5H5N5O/c6-4-3-5(8-1-7-4)9-2-10(3)11/h1-2,10H,(H2,6,7,8)

Upstream product

• 155854-86-7 3-Benzyl-7-oxy-3H-purin-6-ylamine 
• 7280-81-1 3-benzyladenine 
• 66224-66-6 adenine 
• 162714-83-2 1-benzyladenine 7-oxide 

Downstream Products

• 13231-00-0 diceto-6,8 purine 
• 118974-81-5 hypoxanthine 7-N-oxide 
• 5142-23-4 3-methyladenine 

Relevant academic research and scientific papers

Purines. LXVI. Adenine 7-oxide: Its synthesis, chemical properties, and X-ray molecular structure

A detailed account is given of the first unequivocal synthesis of adenine 7-oxide (8). The synthesis started with peroxycarboxylic acid oxidation of 3-benzyladenine (6), readily obtainable from adenine (1) by benzylation, and proceeded through nonreductive debenzylation of the resulting 3-benzyladenine 7-oxide (7). The location of the oxygen function in 7 and 8 was confirmed by their chemical reactions including deamination and methylation and by X-ray crystallographic analysis. A UV spectroscopic approach suggested that the neutral species of 8 exists in H2O as an equilibrated mixture of the NO-oxide (8) and N(7)-OH (21) tautomers. Treatment of 6 with 30% aqueous H2O2 in MeOH in the presence of MeCN and KHCO3 at 30°C produced the N(7)-oxide 7 and 7-acetamido-3-benzyladenine (15) in 12% and 1% yields, respectively.

Purines. LXVII. An alternative synthesis of adenine 7-oxide: N-oxidation of the adenine ring utilizing blocking/deblocking at the 1-position

Oxidation of 1-benzyladenine (12) with m-chloroperoxybenzoic acid in MeOH or in MeOH-1.5 M phosphate buffer (pH 6.6) has been found to afford 1-benzyladenine 7-oxide (13) as the main product. Nonreductive debenzylation of 13 gave adenine 7-oxide (14) in 6

SYNTHESIS OF ADENINE 7-OXIDE FROM ADENINE: UTILIZATION OF A BENZYL GROUP AS A CONTROL SYNTHON AT THE 3-POSITION

The first unequivocal synthetic route to adenine 7-oxide (7) has been established.The route started with peroxycarboxylic acid oxidation of 3-benzyladenine (5), readily obtainable from adenine (2) by benzylation, 8nd proceeded through nonreductive debenzylation of the resulting 3-benzyladenine 7-oxide (6).