79270-98-7

Basic information

• Product Name: 8-azidoadenine
• Synonyms: 8-azidoadenine
• CAS NO: 79270-98-7
• Molecular Formula: C5H4 N8
• Molecular Weight: 0
• Mol File: 79270-98-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 8-azidoadenine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-azidoadenine(79270-98-7)
• EPA Substance Registry System: 8-azidoadenine(79270-98-7)

Safety Data

• Hazardous Substances Data: 79270-98-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H4N8/c6-3-2-4(9-1-8-3)11-5(10-2)12-13-7/h1H,(H3,6,8,9,10,11)

Upstream product

• 6974-78-3 8-bromoadenine 
• 4372-67-2 8-azidoadenosine 
• 131265-35-5 8-Azido-2'-deoxyadenosine 

Downstream Products

• 28128-33-8 8-Aminoadenine 

Relevant articles and documents

Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family

Adenine derivatives bearing substituents in the 2-, N6-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [3H]adenine binding studies at the adenine receptor in rat brain cortical membrane preparations (rAde1R). Steep structure-activity relationships were observed. Substitution in the 8-position (amino, dimethylamino, piperidinyl, piperazinyl) or in the 9-position (2-morpholinoethyl) with basic residues or introduction of polar substituents at the 6-amino function (hydroxy, amino, acetyl) represented the best modifications. Functional evaluation of selected adenine derivatives in adenylate cyclase assays at 1321N1 astrocytoma cells stably expressing the rAde1R showed that all compounds investigated were agonists or partial agonists. A subset of compounds was additionally investigated in binding studies at human embryonic kidney (HEK293) cells, which also express a high-affinity adenine binding site. Structure-affinity relationships at the human cell line were similar to those at the rAde1R, but not identical. In particular, N 6-acetyladenine (25, Ki rat: 2.85 μM; Ki human: 0.515 μM) and 8-aminoadenine (33, Ki rat: 6.51 μM; Ki human: 0.0341 μM) were much more potent at the human as compared to the rat binding site. The new AdeR ligands may serve as lead structures and contribute to the elucidation of the functions of the adenine receptor family. 2009 American Chemical Society.

Hydrolysis of 2'-Deoxypurine Nucleosides. The Effect of Substitution at the C-8 Position.

The hydrolytic stability of 2'-deoxypurine nucleosides is decreased by introduction of electronwithdrawing substituents at the C-8 position in the series of compounds 2-8, 10-14.The sulfone group causes a 2.9 x 104 rate acceleration for glycosidic, bond cleavage in compound 14.