86480-40-2

Basic information

• Product Name: 2-pentofuranosyl-2H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7-diamine
• Synonyms: 2H-1,2,3-triazolo[4,5-d]pyrimidine-5,7-diamine, 2-pentofuranosyl-
• CAS NO: 86480-40-2
• Molecular Formula: C₉H₁₃N₇O₄
• Molecular Weight: 283.244
• Mol File: 86480-40-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 805°C at 760 mmHg
• Flash Point: 440.7°C
• Density: 2.49g/cm³
• Vapor Pressure: 2.3E-27mmHg at 25°C
• Refractive Index: 2.097
• CAS DataBase Reference: 2-pentofuranosyl-2H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-pentofuranosyl-2H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7-diamine(86480-40-2)
• EPA Substance Registry System: 2-pentofuranosyl-2H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7-diamine(86480-40-2)

Safety Data

• Hazardous Substances Data: 86480-40-2(Hazardous Substances Data)

Upstream product

• 61772-86-9 5,7-dimethylsulfanyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 18620-97-8 2,6-diamino-8-azapurine 
• 18646-11-2 α-D-ribofuranosyl-1-phosphate 

Relevant articles and documents

Site-Selective ribosylation of fluorescent nucleobase analogs using purine-Nucleoside phosphorylase as a catalyst: effects of point mutations

Enzymatic ribosylation of fluorescent 8-azapurine derivatives, like 8-azaguanine and 2,6-diamino-8-azapurine, with purine-nucleoside phosphorylase (PNP) as a catalyst, leads to N9, N8, and N7-ribosides. The final proportion of the products may be modulated by point mutations in the enzyme active site. As an example, ribosylation of the latter substrate by wild-type calf PNP gives N7- And N8-ribosides, while the N243D mutant directs the ribosyl substitution at N9- And N7-positions. The same mutant allows synthesis of the fluorescent N7-β-D-ribosyl-8-azaguanine. The mutated form of the E. coli PNP, D204N, can be utilized to obtain non-typical ribosides of 8-azaadenine and 2,6-diamino-8-azapurine as well. The N7- And N8-ribosides of the 8-azapurines can be analytically useful, as illustrated by N7-β-D-ribosyl-2,6-diamino-8-azapurine, which is a good fluorogenic substrate for mammalian forms of PNP, including human blood PNP, while the N8-riboside is selective to the E. coli enzyme.

Synthesis and Biological Evaluation of 2-Fluoro-8-azaadenosine and Related Compounds

The synthesis of 2-fluoro-8-azaadenosine (6e) and 2-amino-8-azaadenosine (6d) is described.Condensation of 9H-2,6-bis(methylthio)-8-azapurine (4) with 2,3,5-tri-O-acetyl-D-ribofuranosyl chloride (5) produces a mixture of 6a (9-β-D-ribofuranosyl) and 7a (8-β-D-ribofuranosyl).Standard functional group manipulation, including a modified Schiemann reaction to introduce the fluorine, allows preparation of 6d and 6e from the major isomer 6a.By a similar series of reactions the minor component 7a was converted to 7d and 7e, with the ribose ring attached at N-8 of the 8-azapurine ring system.Structure proofs utilized UV and 1H and 13C NMR data.Compounds 6b-e,g and 7b-f were evaluated in the H.Ep.-2 cell culture screen, and compounds 6c-e and 7d were evaluated in the P388 mouse leukemia screen.Adenosine deaminase data are also presented for some compounds.