119644-23-4

Basic information

• Product Name: 3'-fluoro-2',3'-dideoxy-5-iodouridine
• Synonyms: 3'-fluoro-2',3'-dideoxy-5-iodouridine;2',3'-Dideoxy-3'-fluoro-5-iodouridine;5-Iodo-3'-fluoro-2',3'-dideoxyuridine;DRE 368
• CAS NO: 119644-23-4
• Molecular Formula: C₉H₁₀FIN₂O₄
• Molecular Weight: 356.09
• Mol File: 119644-23-4.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 2.06g/cm³
• CAS DataBase Reference: 3'-fluoro-2',3'-dideoxy-5-iodouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-fluoro-2',3'-dideoxy-5-iodouridine(119644-23-4)
• EPA Substance Registry System: 3'-fluoro-2',3'-dideoxy-5-iodouridine(119644-23-4)

Safety Data

• Hazardous Substances Data: 119644-23-4(Hazardous Substances Data)

Upstream product

• 699002-92-1 1-((2R,4S,5R)-4-Fluoro-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-iodo-1H-pyrimidine-2,4-dione 
• 41107-56-6 1-(2,3-Dideoxy-3-fluoro-β-D-ribofuranosyl)-uracil 
• 699002-91-0 1-(5-O-trityl-2-deoxy-β-D-lyxofuranosyl)-5-iodoracil 
• 54-42-2 5-Iodo-2'-deoxyuridine 
• 101039-82-1 5-iodo-3'-O-mesyl-5'-O-trityl-2'-deoxyuridine 
• 15414-61-6 2'-deoxy-5-iodo-5'-O-(triphenylmethyl)uridine 
• 75-09-2 dichloromethane 
• 874-60-2 4-methyl-benzoyl chloride 
• 1364916-81-3 5-iodo-[5'-O-(4,4'-dimethoxytrityl)-3'-fluoro]-2',3'-dideoxyuridine 
• 104375-88-4 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-iodouridine 

Relevant articles and documents

Radiolabeled cyclosaligenyl monophosphates of 5-iodo-2′-deoxyuridine, 5-iodo-3′-fluoro-2′,3′-dideoxyuridine, and 3′-fluorothymidine for molecular radiotherapy of cancer: Synthesis and biological evaluation

Targeted molecular radiotherapy opens unprecedented opportunities to eradicate cancer cells with minimal irradiation of normal tissues. Described in this study are radioactive cyclosaligenyl monophosphates designed to deliver lethal doses of radiation to cancer cells. These compounds can be radiolabeled with SPECT- and PET-compatible radionuclides as well as radionuclides suitable for Auger electron therapies. This characteristic provides an avenue for the personalized and comprehensive treatment strategy that comprises diagnostic imaging to identify sites of disease, followed by the targeted molecular radiotherapy based on the imaging results. The developed radiosynthetic methods produce no-carrier-added products with high radiochemical yield and purity. The interaction of these compounds with their target, butyrylcholinesterase, depends on the stereochemistry around the P atom. IC50 values are in the nanomolar range. In vitro studies indicate that radiation doses delivered to the cell nucleus are sufficient to kill cells of several difficult to treat malignancies including glioblastoma and ovarian and colorectal cancers.

Inhibition of Mycobacterium tuberculosis, Mycobacterium bovis, and Mycobacterium avium by novel dideoxy nucleosides

The prevalence of tuberculosis (TB) and mutidrug-resistant tuberculosis (MDR-TB) has been increasing, leading to serious infections, high mortality, and a global health threat. Here, we report the identification of a novel class of dideoxy nucleosides as potent and selective inhibitors of Mycobacterium bovis, Mycobacterium tuberculosis, and drug-resistant Mycobacterium tuberculosis. A series of 5-acetylenic derivatives of 2′,3′-dideoxyuridine (3-8) and 3′-fluoro-2′,3′-dideoxyuridine (22-27) were synthesized and tested for their antimycobacterial activity against M. bovis, M. tuberculosis, and M. avium. 2′,3′-Dideoxyuridine possessing 5-decynyl, 5-dodecynyl, 5-tridecynyl, and 5-tetradecynyl substituents (4-7) exhibited the highest antimycobacterial activity against all three mycobacteria. In contrast, in the 3′-fluoro-2′,3′-dideoxyuridine series, a 5-tetradecynyl analogue (26) displayed the most potent activity against these mycobacteria. Among other derivatives, 5-bromo-2′,3′-dideoxycytidine (11), 5-methyl-2′,3′-dideoxycytidine (12), and 5-chloro-4-thio-2′, 3′-dideoxyuridine (19) exhibited modest inhibition of M. bovis and M. tuberculosis. In the series of dideoxy derivatives of adenosine, guanosine, and purines, 2-amino-6-mercaptoethyl-9-(2,3-dideoxy-β-D-glyceropentofuranosyl) purine (32) and 2-amino-4-fluoro-7-(2,3-dideoxy-β-D-glyceropentofuranosyl) pyrrolo[2,3-d]-pyrimidine (35) were the most efficacious against M. bovis and M. tuberculosis, and M. avium, respectively.

Synthesis and Antiviral Evaluation of Some 3′-Fluoro Bicyclic Nucleoside Analogues

The synthesis of 3′-fluoro analogues of recently discovered highly potent anti-VZV furanopyrimidine deoxynucleosides (BCNAs) is herein reported, for both the alkyl and alkylphenyl series. The compounds are tested against a range of herpes viruses and disp

Method of treating HIV infections with 2',3'-dideoxy-3'-fluoro-5-chlorouridine

A method for treating HIV infections comprising administering a composition whose active ingredient is 2',3'-dideoxy-3'-fluoro-5'-chlorouridine.

Antiviral compounds

2',3'-Dideoxy-3'-fluoro pyrimidine nucleosides particularly 2',3'-dideoxy-3'-fluorothymidine have been found to have particularly potent activity against adenovirus infections especially those caused by adenoviruses of serotype 8. Such compounds are preferably presented in pharmaceutical formulations adapted for ophthalmic administration.