40372-06-3

Basic information

• Product Name: 2'-Deoxyribavirin
• Synonyms: 2'-Deoxyribavirin
• CAS NO: 40372-06-3
• Molecular Formula: C₈H₁₂N₄O₄
• Molecular Weight: 228.20528
• Product Categories: Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 40372-06-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2'-Deoxyribavirin(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-Deoxyribavirin(40372-06-3)
• EPA Substance Registry System: 2'-Deoxyribavirin(40372-06-3)

Safety Data

• Hazardous Substances Data: 40372-06-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2'-Deoxyribavirin is used as an intermediate for the synthesis of 2'-Deoxyribavirin-5'-triphosphate (D249940) for its potential application as a new inhibitor for HIV-1 replication. This makes it a valuable compound in the fight against HIV and AIDS, contributing to the development of novel therapeutic strategies.
Additionally, the triphosphate analog of 2'-Deoxyribavirin can be incorporated with several naturally occurring nucleosides, which further expands its utility in the pharmaceutical industry for the creation of new drugs and therapies.

Upstream product

• 36791-04-5 ribavirin 
• 359861-06-6 C₂₀H₃₈N₄O₅Si₂ 
• 951-78-0 2'-deoxyuridine 
• 3641-08-5 1,2,4-triazole-3-carboxamide 
• 50-89-5 thymidine 

Downstream Products

• 215653-83-1 1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-1H-[1,2,4]triazole-3-carboxylic acid amide 
• 532935-49-2 2'-deoxyribavirin triphosphate 
• 532935-43-6 1-(2'-deoxy-β-D-erythro-pentofuranosyl)-(1H)-1,2,4-triazole-3-carboxamide-5'-tosylate 

Relevant articles and documents

Development of a nanostabilized biocatalyst using an extremophilic microorganism for ribavirin biosynthesis

Ribavirin is a guanosine analogue commonly used as an antiviral compound for the treatment of Hepatitis C virus (HCV) infection. The biosynthesis of this compound using Geobacillus kaustophilus ATCC 8005 as biocatalyst is herein reported. This extremophilic microorganism has been successfully entrapped in an agarose matrix supplemented with bentonite, which was defined as bionanocomposite. This immobilized biocatalyst was stable for more than 580 h without activity loss, significantly improving operational stability and mechanical properties over the conventional agarose matrix. Furthermore, a packed-bed bioreactor for bioprocess scale-up was designed, which was able to produce 370 mg L-1 of ribavirin. In conclusion, a smooth, inexpensive and environmentally friendly method to obtain ribavirin was developed in this study.

Aeromonas hydrophila strains as biocatalysts for transglycosylation

Microbial transglycosylation is useful as a green alternative in the preparation of purine nucleosides and analogues, especially for those that display pharmacological activities. In a search for new transglycosylation biocatalysts, two Aeromonas hydrophila strains were selected. The substrate specificity of both micro-organisms was studied and, as a result, several nucleoside analogues have been prepared. Among them, ribavirin, a broad spectrum antiviral, and the well-known anti HIV didanosine, were prepared, in 77 and 62% yield using A. hydrophila CECT 4226 and A. hydrophila CECT 4221, respectively. In order to scale-up the processes, the reaction conditions, product purification and biocatalyst preparation were analyzed and optimized.

In search of new inhibitors of HIV-1 replication: Synthesis and study of 1-(2′-deoxy-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide as a selective viral mutagenic agent

With the emergence of HIV strains resistant or cross-resistant to nearly all antiretroviral regimen, novel therapy approaches have to be considered. As a part of our current work on viral mutagenic compounds, we prepared 1-(2′-deoxy-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide (2′-deoxy-ribavirin) and its 5′-triphosphate derivative. The nucleoside mutagenic activity was evaluated on HIV-1 NL4-3 in CEMx174 cell culture. After 2.5 months, no reduction on HIV-1 viability was observed. On the other hand, in vitro experiments with purified HIV-1 RT demonstrated that the triphosphate analog can be incorporated opposite to several natural nucleosides. Copyright Taylor & Francis Group, LLC.

Imidazole-4-carboxamide and 1,2,4-triazole-3-carboxamide deoxynucleotides as simplified DNA building blocks with ambiguous pairing capacity

2'-Deoxynucleosides of imidazole-4 (or 1,2,4-triazole-3)-carboxamide, ethyl imidazole-4 (or 1,2,4-triazole-3)-carboxylate were synthesized by enzymatic glycosylation using N-deoxyribosyltransferase from a lactobacterium. The base pairing properties of Y and V when placed opposite the natural DNA bases as well as their serf were evaluated by thermal denaturation experiments. DNA templates containing imidazole-4-carboxamide base were used in elongation reaction catalysed by Klenow fragment.