1445385-02-3

Usage

Uses

Used in Medicinal Chemistry:
4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine is used as a precursor in the synthesis of antiviral and anticancer agents for its potential to inhibit viral replication and tumor growth. Its unique structural features may provide a basis for the development of novel therapeutic agents with improved efficacy and selectivity.
Used in Antiviral Drug Development:
In the pharmaceutical industry, 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine is used as a key intermediate in the development of antiviral drugs, leveraging its ability to interfere with viral replication processes and offering a new avenue for treating viral infections.
Used in Anticancer Drug Development:
Similarly, in oncology, 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine is utilized as a building block for the creation of anticancer drugs, with the aim of targeting cancer cells while minimizing damage to healthy cells, thus improving treatment outcomes for cancer patients.
Used in Research and Development:
In the field of biological research, 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine serves as a valuable tool for studying the interactions of nucleoside analogs with biological macromolecules, providing insights into their mechanisms of action and potential applications in therapeutic interventions.

Upstream product

• 1445379-88-3 C₃₂H₄₄ClFN₂O₅Si₂ 
• 1445379-64-5 3'-O-(tert-butyldimethylsilyl)-5′-O-(tert-butyldiphenylsilyl)-2′-deoxy-2′-fluoro-4′-hydroxymethyluridine 
• 1445379-61-2 4'-α-methylhydroxyl-3'-tert-butyldimethylsilyl-2'-deoxy-2'-fluorouridine 
• 1445379-59-8 2’-deoxy-2’-fluoro-3’-O-(tert-butyldimethylsilyl)uridine 
• 1445379-90-7 C₃₂H₄₅ClFN₃O₄Si₂ 
• 1445385-00-1 C₃₈H₄₁ClFN₃O₇ 
• 1445382-55-7 C₃₀H₂₉ClFN₃O₅ 
• 97-72-3 2-Methylpropionic anhydride 

Relevant academic research and scientific papers

Discovery of 4′-chloromethyl-2′-deoxy-3′,5′-di- O -isobutyryl-2′-fluorocytidine (ALS-8176), A first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection

Respiratory syncytial virus (RSV) is a leading pathogen of childhood and is associated with significant morbidity and mortality. To date, ribavirin is the only approved small molecule drug, which has limited use. The only other RSV drug is palivizumab, a monoclonal antibody, which is used for RSV prophylaxis. Clearly, there is an urgent need for small molecule RSV drugs. This article reports the design, synthesis, anti-RSV activity, metabolism, and pharmacokinetics of a series of 4′-substituted cytidine nucleosides. Among tested compounds 4′-chloromethyl-2′-deoxy-2′-fluorocytidine (2c) exhibited the most promising activity in the RSV replicon assay with an EC50 of 0.15 μM. The 5′-triphosphate of 2c (2c-TP) inhibited RSV polymerase with an IC50 of 0.02 μM without appreciable inhibition of human DNA and RNA polymerases at 100 μM. ALS-8176 (71), the 3′,5′-di-O-isobutyryl prodrug of 2c, demonstrated good oral bioavailability and a high level of 2c-TP in vivo. Compound 71 is a first-in-class nucleoside RSV polymerase inhibitor that demonstrated excellent anti-RSV efficacy and safety in a phase 2 clinical RSV challenge study.

SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF

Disclosed herein are nucleosides, nucleotides and analogs thereof, pharmaceutical compositions that include one or more of nucleosides, nucleotides and analogs thereof, and methods of synthesizing the same. Also disclosed herein are methods of ameliorating and/or treating a disease and/or a condition, including an infection from a paramyxovirus and/or an orthomyxovirus, with a nucleoside, a nucleotide and an analog thereof.