28128-32-7

Usage

Uses

Used in Pharmaceutical Research:
8-Methoxy-5H-purin-6-amine is used as a biological probe for studying various cellular processes, particularly those involving purine metabolism and signaling pathways. Its unique structure allows researchers to investigate the role of purines in cellular functions and their potential as therapeutic targets.
Used in Drug Discovery and Development:
Due to its potential pharmacological applications, such as antiviral and antitumor properties, 8-Methoxy-5H-purin-6-amine is a focus of interest in drug discovery and development. Its ability to target specific cellular processes makes it a promising candidate for the development of new therapeutic agents to treat various diseases.

InChI:InChI=1/C6H7N5O/c1-12-6-10-3-4(7)8-2-9-5(3)11-6/h2-3H,1H3,(H2,7,8,9,10,11)

Upstream product

• 127133-09-9 2',3'-Dideoxy-8-methoxyadenosine 
• 124-41-4 sodium methylate 
• 6974-78-3 8-bromoadenine 
• 19916-15-5 6,8-dichloro-7(9)H-purine 
• 13231-00-0 diceto-6,8 purine 
• 28128-28-1 8-chloroadenine 
• 185201-10-9 3-Benzyl-8-methoxy-3H-purin-6-ylamine 

Relevant academic research and scientific papers

Purines. LXXIV. Syntheses and rearrangements of 8-oxoadenines monomethylated at the N6-, 1-, and 3-positions

On treatment with boiling 2N hydrochloric acid for 48h, N6-methyl-8- oxoadenosine (1), 1-methyl-8-oxnadenosine (5), and 7-methyl-8-oxoadenosine (8) underwent glycosidic hydrolysis, though much more slowly than the corresponding 8-unsubstituted compounds, furnishing the aglycons (2, 6, and 9) in 45%-63% yields. Under these conditions, N6-methyl-8-oxoadenine (2) rearranged to 9-methyl-8-oxoadenine (3) (8% yield), presumably through fission and reclosure of the imidazole ring. Apparent methyl migration also occurred with 3-methyl-8-hydroxyadenine (7), which afforded 1-methyl-8- oxoadenine (6) in 9% yield on treatment with hydrochloric acid under similar conditions.

A chemical switch for transforming a purine agonist for toll-like receptor 7 to a clinically relevant antagonist

Toll-like receptor 7 (TLR7) is an established therapeutic target in myriad autoimmune disorders, but no TLR7 antagonist is available for clinical use to date. Herein, we report a purine scaffold TLR7 antagonist, first-of-its-kind to our knowledge, which was developed by rationally dissecting the structural requirements for TLR7-targeted activity for a purine scaffold. Specifically, we identified a singular chemical switch at C-2 that could make a potent purine scaffold TLR7 agonist to lose agonism and acquire antagonist activity, which could further be potentiated by the introduction of an additional basic center at C-6. We ended up developing a clinically relevant TLR7 antagonist with favorable pharmacokinetics and 70.8% oral bioavailability in mice. Moreover, the TLR7 antagonists depicted excellent selectivity against TLR8. To further validate the in vivo applicability of this novel TLR7 antagonist, we demonstrated its excellent efficacy in preventing TLR7-induced pathology in a preclinical murine model of psoriasis.