1496551-72-4

Basic information

• Product Name: 1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione
• Synonyms: 1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione;EOS-61178;(2'R)-2'-Chloro-2'-deoxy-2'-methyl-uridine;sofosbuvir (2’R)-2’-Chloro-2’-deoxy-2’-methyl-uridine;1-[(2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• CAS NO: 1496551-72-4
• Molecular Formula: C₁₀H₁₃ClN₂O₅
• Molecular Weight: 276.67362
• Mol File: 1496551-72-4.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione(1496551-72-4)
• EPA Substance Registry System: 1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione(1496551-72-4)

Safety Data

• Hazardous Substances Data: 1496551-72-4(Hazardous Substances Data)

Usage

Description

1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione is a complex organic compound with a unique molecular structure. It is characterized by its tetrahydrofuran ring with a chloro and hydroxymethyl group, as well as a pyrimidine ring with a 2,4-dione functional group. 1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione has potential applications in various fields due to its specific structural features and chemical properties.

Uses

Used in Pharmaceutical Industry:
1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione is used as a potential therapeutic agent for the treatment of various diseases. Its unique molecular structure allows it to interact with specific biological targets, making it a promising candidate for drug development.
Used in Antiviral Applications:
As a possible metabolite of Sofosbuvir, this compound is being investigated for its potential use in the treatment of hepatitis C. It is metabolized to the active antiviral agent 2''-deoxy-2''-α-fluoro-β-C-methyluridine-5''-monophosphate, which has shown effectiveness in combating the hepatitis C virus.
Used in Drug Development Research:
The compound's unique structure and potential biological activity make it an interesting subject for further research in drug development. It can be studied for its interactions with various biological targets and its potential to be modified or optimized for specific therapeutic applications.
Used in Chemical Synthesis:
Due to its complex structure, 1-((2R,3R,4R,5R)-3-chloro-4-hydroxy-5-(hydroxyMethyl)-3-Methyltetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione can also be used as a starting material or intermediate in the synthesis of other complex organic compounds, potentially leading to the development of new drugs or chemical products.

Upstream product

• 1496551-71-3 C₂₄H₂₁ClN₂O₇ 
• 1496551-70-2 2'-deoxy-2'-chloro-2'-C-methyl-3',5'-di-O-benzoyl-N⁴-benzoylcytidine 
• 31448-54-1 2'-C-methyluridine 
• 944476-40-8 (2R,3R,3aS,9aR)-3-hydroxy-2-(hydroxymethyl)-3a-methyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one 
• 83159-91-5 3,5-di-O-(tert-butyldimethylsilyl)-2-deoxy-D-ribono-1,4-lactone 
• 119410-95-6 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylenetetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 
• 879551-01-6 (4S,5R)-ethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-meth-yl-1,3,2-dioxathiolane-4-carboxylate 2,2-dioxide 

Downstream Products

• 1613590-78-5 C₁₇H₁₅ClFIN₂O₅ 
• 1613590-79-6 C₁₇H₁₆ClFN₂O₆ 
• 1613590-91-2 C₂₂H₂₈ClFN₃O₉P 
• 1496551-77-9 MK-3682 
• 1496551-77-9 ((S)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-chloro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-D-alanine isopropyl ester 

Relevant articles and documents

Synthesis and Anti-HCV Activities of 4′-Fluoro-2′-Substituted Uridine Triphosphates and Nucleotide Prodrugs: Discovery of 4′-Fluoro-2′- C-methyluridine 5′-Phosphoramidate Prodrug (AL-335) for the Treatment of Hepatitis C Infection

We report the synthesis and biological evaluation of a series of 4′-fluoro-2′-C-substituted uridines. Triphosphates of the uridine analogues exhibited a potent inhibition of hepatitis C virus (HCV) NS5B polymerase with IC50 values as low as 27 nM. In an HCV subgenomic replicon assay, the phosphoramidate prodrugs of these uridine analogues demonstrated a very potent activity with EC50 values as low as 20 nM. A lead compound AL-335 (53) demonstrated high levels of the nucleoside triphosphate in vitro in primary human hepatocytes and Huh-7 cells as well as in dog liver following a single oral dose. Compound 53 was selected for the clinical development where it showed promising results in phase 1 and 2 trials.

PROCESS FOR MAKING CHLORO-SUBSTITUTED NUCLEOSIDE PHOSPHORAMIDATE COMPOUNDS

The present invention is directed to a process for making Chloro-Substituted Nucleoside Phosphoramidate Compounds of formula (I): which are useful for the treatment and prophylaxis of HCV infection. The present invention is also directed to compounds that are useful as synthetic intermediates for making the compounds of formula (I).

Deuterated HCV NS5b inhibitor nucleotide derivative and application thereof

The invention provides a deuterated HCV (Hepatitis C Virus) NS5b inhibitor nucleotide derivative or its pharmaceutically acceptable salts, stereoisomers, tautomer inhibitors and its application in preparation of drugs for treatment or prevention of HCV infection. The inhibitor is represented by a general formula I (shown in the description).