185201-05-2

Usage

Structure

Contains a purine ring

Functional Groups

Amino group at the 6th position
Phenylmethyl group at the 3rd position

Classification

Purine derivative

Nature

Organic compound

Structure Type

Heterocyclic

Biological Activities

Synthesis of Nucleotide Analogs: Potential involvement
Drug Target: Under investigation for various diseases

Applications

Pharmaceutical Research: Interest as a subject of study
Medicinal Chemistry: Potential for drug development and therapeutic agents

Upstream product

• 155854-86-7 3-Benzyl-7-oxy-3H-purin-6-ylamine 
• 185201-10-9 3-Benzyl-8-methoxy-3H-purin-6-ylamine 

Relevant academic research and scientific papers

The 7-N-oxides of purines related to nucleic acids: Their chemistry, synthesis, and biological evaluation

Recent advances in the chemistry, synthesis, and biological evaluation of the 7-N-oxides of purines related to nucleic acids are reviewed. The 7-N-oxides covered are those of guanine (1), adenine (2), and hypoxanthine (3) and of related compounds such as

Purines. LXXIII. Syntheses of 8-alkoxy- and 8-hydroxy-3-alkyladenines from 3-alkyladenine 7-oxides through 7-alkoxy-3-alkyladenines

7-Alkoxy-3-alkyladenine perchlorates (9) were prepared from 3- alkyladenines (4) by N-oxidation followed by alkylation with alkyl halides in N,N-dimethylacetamide. The 7-methoxy derivatives 9d,g,j thus obtained afforded 3-methyl-8-hydroxyadenine (7a), 3-ethyl-8-hydroxyadenine (7b), and 3-benzyl-8-hydroxyadenine (7c) in 74%, 72%, and 39% yields, respectively, on treatment with boiling 0.1 N aqueous sodium hydroxide, whereas treatment of 9d, g, j with sodium methoxide in methanol at room temperature afforded 3- alkyl-8-methoxyadenines (10m, p,q) in 91%-98% yields. Similar treatment of 9d with sodium ethoxide in ethanol afforded 8-ethoxy-3-methyladenine (10n) in 89% yield. Compounds 10m, q were alternatively prepared from 9d,j in 77% and 84% yields, respectively, by treatment with 0.1 N aqueous sodium hydroxide in the presence of methanol. This method was suitable for the synthesis of the 8-benzyloxy compound too: it was obtained in 60% yield by treating 7- benzyloxy-3-methyladenine perchlorate (9f) with a mixture of aqueous sodium hydroxide and benzyl alcohol. Compounds 7 were alternatively prepared from 9 through 10. For example, 7c was obtained in 84% overall yield by treatment of 9j with sodium methoxide, followed by hydrolysis of the resulting 10q with boiling 1 N hydrochloric acid. On the other hand, methylation of 3- methyladenine 7-oxide (8a) with dimethyl sulfate in 0.1 N aqueous sodium hydroxide in the absence or presence of added methanol afforded N6,3- dimethyladenine 7-oxide (14) in 13% or 14% yield, together with 7a (4% yield) or 10m (11%).