1333126-30-9

Basic information

• Product Name: 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil
• Synonyms: 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil
• CAS NO: 1333126-30-9
• Molecular Weight: 529.869
• Mol File: 1333126-30-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil(1333126-30-9)
• EPA Substance Registry System: 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil(1333126-30-9)

Safety Data

• Hazardous Substances Data: 1333126-30-9(Hazardous Substances Data)

Usage

Description

1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil is a complex organic compound with a unique chemical structure. It is characterized by its azido, deoxy, and fluoro functional groups, as well as its benzoyl and chlorobenzoyl ester moieties. This molecule has potential applications in the pharmaceutical and medical fields due to its specific structural features.

Uses

1. Used in Antiviral Applications:
1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil is used as a reactant for the preparation of 2''-deoxy-2''-fluoro-4''-azido nucleoside analogs, which have demonstrated extremely potent anti-HIV activity against various viral strains, including NL4-3 (wild-type), NL4-3 (K101E), and RTMDR. Its application in this field is due to its ability to inhibit the replication of the HIV virus, providing a potential therapeutic option for patients suffering from HIV.
2. Used in Antiviral Synthesis for Hepatitis B:
In the pharmaceutical industry, 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil is also utilized for the synthesis of 4-substituted fluoronucleoside analogs. These analogs are specifically designed for the treatment of Hepatitis B virus infection. The compound's role in this application is attributed to its potential to interfere with the viral replication process, thereby offering a therapeutic approach to combat Hepatitis B.

Upstream product

• 491594-58-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranose 
• 173379-67-4 1-(4-azido-2,5-dideoxy-2-fluoro-5-iodo-β-D-arabino-furanosyl)uracil 
• 98-88-4 benzoyl chloride 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 69123-94-0 1-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)uracil 
• 128496-10-6 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)uracil 
• 97614-44-3 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide 
• 1145869-36-8 1-(4'-azido-3'-O-benzoyl-2'-deoxy-2'-fluoro-5'-iodo-β-D-arabinofuranosyl)uracil 
• 535-80-8 3-chlorobenzoate 
• 173379-64-1 4′,5′-didehydro-2′,5′-dideoxy-2′-fluoroarabinouridine 
• 173379-62-9 1-(2,5-dideoxy-2-fluoro-5-iodo-β-D-arabino-furanosyl)uracil 

Downstream Products

• 1011529-10-4 4′-azido-2′-deoxy-2′-fluoro-β-D-arabinocytidine 
• 173379-73-2 1-((2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydro-furan-2-yl)pyrimidine-2,4(1H,3H)-dione 
• 1360459-58-0 C₃₈H₃₉ClFN₅O₉S 
• 1360459-71-7 C₂₉H₂₆ClFN₆O₈ 
• 1360459-70-6 C₂₈H₂₅ClFN₇O₉ 
• 1360459-69-3 C₂₅H₂₁ClFN₇O₇ 
• 1360459-68-2 C₂₇H₂₄ClFN₆O₈S 
• 1360459-67-1 C₂₇H₂₄ClFN₆O₉ 
• 1360459-66-0 C₂₉H₂₈ClFN₆O₈S 
• 1360459-65-9 C₂₉H₂₈ClFN₆O₈ 
• 1360459-64-8 C₂₉H₂₆ClFN₆O₁₀ 

Relevant articles and documents

3-methyl uridine and 4-methyl cytidine nucleoside compound, synthetic method and its pharmaceutical use

The invention discloses a 3-methyluridine and 4-methylcytidine nucleosides compound and a synthesis method and pharmaceutical application thereof, belonging to the field of medicinal chemistry. The compound has a structural formula as shown in the specification. The compound has the effects of simultaneously modifying sugar rings and basic groups, increasing the activity of the compound and reducing the toxicity, provides a good application prospect for development of like medicines and can be applied to preparation of anti-HBV (Hepatitis B virus) medicines. The synthesis method is simple and feasible and provides conditions for mass synthesis of the compound.

Synthesis of new 2′-deoxy-2′-fluoro-4′-azido nucleoside analogues as potent anti-HIV agents

We prepared 1-(4′-azido-2′-deoxy-2′-fluoro-β-d- arabinofuranosyl)cytosine (10) and its hydrochloride salt (11) as potential antiviral agents based on the favorable antiviral profiles of 4′-substituted nucleosides. Compounds 10 and 11 were synthesized from 1,3,5-O-tribenzoyl-2-deoxy-2-fluoro-d-arabinofuranoside in multiple steps, and their structures were unequivocally established by IR, 1H NMR, 13C NMR, and 19F NMR spectroscopy, HRMS, and X-ray crystallography. Compounds 10 and 11 exhibited potent anti-HIV-1 activity (EC50: 0.3 and 0.13 nM, respectively) without significant cytotoxicity in concentrations up to 100 μM. Compound 11 exhibited extremely potent anti-HIV activity against NL4-3 (wild-type), NL4-3 (K101E), and RTMDR viral strains, with EC50 values of 0.086, 0.15, and 0.11 nM, respectively. Due to the high potency of 11, it was also screened against an NIH Reagent Program NRTI-resistant virus panel containing eleven mutated viral strains and for cytotoxicity against six different human cell lines. The results of this screening indicated that 11 is a novel NRTI that could be developed as an anti-AIDS clinical trial candidate to overcome drug-resistance issues.