211694-25-6

Basic information

• Product Name: 2',5'-Dideoxy-2'-fluoro-5'-iodouridine
• Synonyms: 2',5'-Dideoxy-2'-fluoro-5'-iodouridine;1-(2,5-Dideoxy-2-fluoro-5-iodo-beta-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione
• CAS NO: 211694-25-6
• Molecular Formula: C9H10FIN2O4
• Molecular Weight: 356.0895732
• Mol File: 211694-25-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2',5'-Dideoxy-2'-fluoro-5'-iodouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',5'-Dideoxy-2'-fluoro-5'-iodouridine(211694-25-6)
• EPA Substance Registry System: 2',5'-Dideoxy-2'-fluoro-5'-iodouridine(211694-25-6)

Safety Data

• Hazardous Substances Data: 211694-25-6(Hazardous Substances Data)

Usage

Uses

2''-Fluoro-5''-iodo deoxyuridine can be used in synthetic preparation of substituted nucleosides, nucleotides and analogs thereof as antiviral agents.

Upstream product

• 157024-77-6 9-<2-deoxy-2-fluoro-3,5-di-O-(tetrahydropyran-2-yl)-β-D-ribofuranosyl>uracil 
• 157024-75-4 9-<3,5-di-O-(tetrahydropyran-2-yl)-β-D-arabinofuranosyl>uracil 
• 351523-07-4 3',5'-di-O-(tetrahydropyran-2-yl)-2,2'-O-cyclouridine 
• 3736-77-4 2,2'-Anhydrouridine 
• 58-96-8 uridine 
• 56287-17-3 2'-deoxy-2'-fluorouridine 

Downstream Products

• 1612841-23-2 1-(3,5-di-O-benzoyl-2-deoxy-2,4-difluoro-β-D-ribofuranosyl)uracil 
• 1612841-21-0 1-(5-O-benzoyl-2-deoxy-2,4-difluoro-β-D-ribofuranosyl)uracil 
• 1612841-19-6 1-(3-O-benzoyl-2-deoxy-2,4-difluoro-5-iodo-β-D-ribofuranosyl)-uracil 
• 1445381-05-4 C₃₁H₂₆FN₃O₈ 
• 1445381-01-0 C₂₄H₂₁FN₂O₈ 
• 1445380-99-3 3'-O-benzoyl-2',5'-dideoxy-2'-fluoro-5'-iodo-4'-Cα-methoxyuridine 
• 1445380-93-7 C₃₂H₃₄FN₃O₅ 
• 1445380-91-5 C₄₄H₆₂FN₃O₅Si₂ 
• 1445380-87-9 C₄₄H₆₀FN₃O₅Si₂ 

Relevant articles and documents

Modified nucleoside, nucleotide and modified nucleic acid polymer as well as preparation method and application thereof

The invention relates to the technical field of nucleic acid medicines, in particular to modified nucleoside, nucleotide and a modified nucleic acid polymer as well as a preparation method and application thereof. The modified nucleoside is selected from

Azido nucleosides and nucleotide analogs

Disclosed herein are 4′-azido-substituted nucleosides, nucleotides and analogs thereof, pharmaceutical compositions that include one or more of 4′-azido-substituted 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 4′-azido-substituted nucleoside, a nucleotide and/or an analog thereof. Examples of viral infections include a respiratory syncytial viral (RSV) and influenza infection.

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.