20535-04-0

Basic information

• Product Name: 9-(5-deoxypent-4-enofuranosyl)-9H-purin-6-amine
• CAS NO: 20535-04-0
• Molecular Formula: C₁₀H₁₁N₅O₃
• Molecular Weight: 249.226
• Mol File: 20535-04-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 591.1°C at 760 mmHg
• Flash Point: 311.3°C
• Density: 1.91g/cm³
• Vapor Pressure: 8.14E-15mmHg at 25°C
• Refractive Index: 1.867
• CAS DataBase Reference: 9-(5-deoxypent-4-enofuranosyl)-9H-purin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(5-deoxypent-4-enofuranosyl)-9H-purin-6-amine(20535-04-0)
• EPA Substance Registry System: 9-(5-deoxypent-4-enofuranosyl)-9H-purin-6-amine(20535-04-0)

Safety Data

• Hazardous Substances Data: 20535-04-0(Hazardous Substances Data)

Upstream product

• 79849-80-2 Desoxy-5'-o-nitrophenylselenyl-5'adenosine 
• 79849-81-3 Desoxy-5'o-nitrophenylselenoxy-5'adenosine 
• 4099-81-4 5'-iodo-5'-deoxyadenosine 
• 58-61-7 adenosine 

Downstream Products

• 157031-43-1 2',3',N,N-tetrabenzoyl-4',5'-didehydro-5'-deoxyadenosine 
• 68200-73-7 6-N-benzoyl-9-(5-deoxy-β-D-erythro-pent-4-enofuranosyl)adenine 

Relevant articles and documents

First example of phosphoramidate approach applied to a 4′-substituted purine nucleoside (4′-Azidoadenosine): Conversion of an inactive nucleoside to a submicromolar compound versus hepatitis C virus

We report on the synthesis of the anti hepatitis C virus (HCV) agent 4′-azidoadenosine (1) and the application of the phosphoramidate ProTide technology to this nucleoside. The synthesis of 1 was achieved through an epoxide intermediate followed by regio- and stereoselective ring opening by azidotrimethylsilane in the presence of a Lewis acid. Compound 1 did not inhibit HCV replication in cell culture at concentrations up to 0.1 mM. However, a submicromolar active agent could be derived from 1 by the application of the ProTide technology. All the phosphoramidates prepared were L-alanine derivatives with variations in the aryl moiety and in the ester part of the amino acid. The benzyl ester and the 1-naphthyl phosphate (18) had the best activity in replicon assay. Phosphoramidates (18-21) achieved a significant improvement in antiviral potency over the parent nucleoside (1) with no increase in cytotoxicity.

Synthesis and hybridizing property of oligonucleotides including 2′-C,4′-Cethyleneoxy- bridged 2′-deoxyadenosine with an exocyclic methylene unit

2′,4′-Bridged nucleic acids (2′,4′-BNAs) are of interest because oligonucleotides that include them have excellent duplex-forming capability and high nuclease resistance compared to natural oligonucleotides. We have recently developed 2′-C,4′-C-ethyleneoxy-bridged thymidine with an exocyclic methylene unit (methylene-EoDNA-T) as a novel 2′,4′-BNA analog. Oligonucleotides that include methylene-EoDNA-T have marked hybridizing capability, nuclease resistance, and in vitro gene-silencing potency. In the present study, we designed and synthesized a 2′-deoxyadenosine analog of methylene-EoDNA (methylene-EoDNA-A), and incorporated it into oligonucleotides. The results of melting temperature (Tm) analysis of duplexes formed from methylene-EoDNA-A-modified oligonucleotides indicated that the hybridizing capability with regard to complementary DNA was almost the same or slightly higher than that of natural DNA. Moreover, methylene-EoDNA-A:methylene-EoDNA-T base pairs increased the thermal stability of DNA duplexes compared to that of DNA duplexes containing methylene-EoDNA-A- or methylene-EoDNA-T-modification in one strand.

Antiviral phosphoramidates

The invention provides novel nucleoside compounds of formula I wherein R1, R2a, R2b, R3, R4, R5, R6, R8a, R9 and R10 are as defined herein which are useful for the treatment of Hepatitis C Virus (HCV) mediated diseases. The invention further provides methods for treatment or prophylaxis of HCV mediated diseases with compounds of formula I and pharmaceutical compositions comprising these compounds,