7013-16-3

Basic information

• Product Name: HYPOXANTHINE-9-BETA-D-ARABINOFURANOSIDE
• Synonyms: 9-BETA-D-ARABINOFURANOSYL-HYPOXANTHINE;HYPOXANTHINE-9-BETA-D-ARABINOFURANOSIDE;9-beta-D-arabinofuranosyl-1,9-dihydro-6H-purin-6-one;ARABINOFURANOSYL-HYPOXANTHINE;9-β-D-Arabinofuranosyl hypoxanthine;9-(b-D-Arabinofuranosyl)hypoxanthine;Arabinosylhypoxanthine;hypoxanthine arabinoside
• CAS NO: 7013-16-3
• Molecular Formula: C₁₀H₁₂N₄O₅
• Molecular Weight: 268.23
• EINECS: 230-295-3
• Mol File: 7013-16-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 732.8°Cat760mmHg
• Flash Point: 397°C
• Appearance: /
• Density: 2.08g/cm³
• Vapor Pressure: 1.52E-22mmHg at 25°C
• Refractive Index: 1.879
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Water (Slightly)
• PKA: 8.92±0.70(Predicted)
• CAS DataBase Reference: HYPOXANTHINE-9-BETA-D-ARABINOFURANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: HYPOXANTHINE-9-BETA-D-ARABINOFURANOSIDE(7013-16-3)
• EPA Substance Registry System: HYPOXANTHINE-9-BETA-D-ARABINOFURANOSIDE(7013-16-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 7013-16-3(Hazardous Substances Data)

Usage

Description

HYPOXANTHINE-9-BETA-D-ARABINOFURANOSIDE, also known as Aranosine, is a nucleoside derivative that plays a significant role in the pharmaceutical industry. It is characterized by its unique chemical structure, which consists of a hypoxanthine base attached to a beta-D-arabinofuranoside sugar moiety. This structure allows it to interact with various biological systems and contribute to the development of novel therapeutic agents.

Uses

Used in Pharmaceutical Industry:
HYPOXANTHINE-9-BETA-D-ARABINOFURANOSIDE is used as an intermediate compound for the synthesis of various antiviral and anticancer drugs. Its unique chemical structure makes it a valuable building block in the development of new pharmaceuticals with improved efficacy and reduced side effects.
Used in Antiviral Drug Development:
HYPOXANTHINE-9-BETA-D-ARABINOFURANOSIDE is used as a key component in the preparation of 5''-O-D-valyl adenine 9-β-D-arabinofuranoside, a potential prodrug for improving the oral bioavailability of the antiviral agent Vidarabine (V305030). This application aims to enhance the effectiveness of Vidarabine in treating viral infections by increasing its bioavailability and reducing the need for frequent injections.

InChI:InChI=1/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7+,10-/m1/s1

Upstream product

• 3083-77-0 araU 
• 68-94-0 Allopurinol 
• 5536-17-4 arabinosyl adenine 
• 38819-10-2 9-β-D-arabinofuranosylguanine 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 68-94-0 hypoxanthine 
• 58-63-9 inosine 
• 108321-99-9 α,β-D-arabinofuranose-5-phosphate disodium salt 
• 69275-14-5 ethyl 5-amino-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazole-4-carboxylate 
• 37776-25-3 2,3,5-tri-O-benzyl-D-arabinose 
• 4060-34-8 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride 
• 52522-49-3 2,3,5-tri-O-benzyl-1-(4-nitrobenzoyloxy)-D-arabinofuranose 

Downstream Products

• 31504-19-5 1-benzylinosine 
• 110505-76-5 6-(3-hydroxybenzylamino)-9-β-D-arabinofuranosylpurine 
• 5987-73-5 (2R,3R,4S,5R)-2-(acetoxymethyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 99236-81-4 Toluene-4-sulfonic acid (R)-2-(1-benzyl-6-oxo-1,6-dihydro-purin-9-yl)-2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-ethoxy]-ethyl ester 
• 99236-80-3 1-Benzyl-9-{(S)-1-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-ethoxy]-2-hydroxy-ethyl}-1,9-dihydro-purin-6-one 
• 99236-78-9 1-benzyl-5'-O-tert-butyldimethysilylinosine 
• 99236-82-5 1-benzyl-6-oxo-9-<(2R,6R)-6-tertbutyldimethylsilyloxymethyl-1-oxa-4-thiacyclohexane-2-yl>-9H-purine 
• 99051-98-6 1-benzyl-6-oxo-9-<(2R,6R)-6-hydroxymethyl-1-oxa-4-thiacyclohexan-2-yl>-9H-purine 
• 68-94-0 Allopurinol 
• 72075-46-8 O¹-Phosphono-α-D-arabinofuranose 
• 1187-84-4 S-methyl-L-cysteine 
• 2140-73-0 1-methylinosine 

Relevant articles and documents

5′-O-D-valyl ara A, a potential prodrug for improving oral bioavailability of the antiviral agent vidarabine

In order to improve the oral bioavailability of Adenine 9-β-D-arabinofuranoside (Vidarabine, also called ara A), an antiviral drug which is active against herpes simplex and varicella zoster viruses and the first agent to be licensed for the treatment of

The arsenolysis reaction in the biotechnological method of synthesis of modified purine β-D-arabinonucleosides

We found a unique property of E. coli purine nucleoside phosphorylases to selectively perform the arsenolysis reaction of ribonucleosides in their active site without affecting β-D-arabinonucleosides. In the synthesis of modified β-D-arabinonucleosides from the corresponding ribonucleosides, the catalytical amount of sodium arsenate in the transglycosylation reaction provided a 95 to 98% conversion rate. Such an approach was shown to simplify the composition of the reaction mixtures and facilitate the isolation of the target nucleosides, particularly, vidarabine, fludarabine, and nelarabine.

Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase

The present invention provides nucleoside compounds and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such nucleoside compounds alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the nucleoside compounds of the present invention.