119644-22-3

Usage

Uses

Used in Antiviral Applications:
5-CHLORO-2',3'-DIDEOXY-3'-FLUORO-URIDINE is used as an antiviral agent for its activity against HIV-1 and HIV-2 in vitro. It exerts its antiviral effects by inhibiting the replication of the virus, thereby reducing the viral load and preventing the progression of the infection.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-CHLORO-2',3'-DIDEOXY-3'-FLUORO-URIDINE is used as a key intermediate in the synthesis of other antiviral drugs. Its unique chemical structure allows for the development of novel therapeutic agents with improved antiviral activity and reduced side effects.
Used in Research and Development:
5-CHLORO-2',3'-DIDEOXY-3'-FLUORO-URIDINE is also used in research and development for the study of viral replication mechanisms and the development of new antiviral strategies. Its unique chemical properties make it a valuable tool for understanding the molecular interactions between the virus and its host cells, as well as for the design of new antiviral compounds with enhanced efficacy and selectivity.

Upstream product

• 171074-97-8 (2R,4S,5R)-5-chloro-1-<5-(1,3-diphenyl-2-imidazolidinyl)-4-fluoro-tetrahydro-2-furyl>uracil 
• 171074-96-7 5-chloro-1-(2,3-dideoxy-3-fluoro-β-D-erythro-pentodialdofuranosyl)uracil 
• 121626-80-0 5'-O-acetyl-2',3'-dideoxy-3'-fluoro-5-chlorouridine 

Downstream Products

• 171074-97-8 (2R,4S,5R)-5-chloro-1-<5-(1,3-diphenyl-2-imidazolidinyl)-4-fluoro-tetrahydro-2-furyl>uracil 

Relevant academic research and scientific papers

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.

Synthesis of tritium-labelled 5-chloro-2',3'-dideoxy- 3'-fluorouridine (935U83) - A selective anti-HIV agent

[5'-3H]-5-Chloro-2',3'-dideoxy-3'-fluorouridine (1; R=[3H]) was prepared at a specific activity of 10.2 Ci/mmol suitable for development of a radioimmunoassay procedure. The synthetic sequence employed controlled oxidation of unlabelled 1 to the 5'-aldehyde (2), isolation as the imidazolidine adduct (3), regeneration of the free aldehyde, reduction with [3H]NaBH4, and purification by preparative TLC. The radiochemical purity was 98.0%.

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.

Synthesis and Anti-HIV Evaluation of 2',3'-Dideoxyribo-5-chloropyrimidine Analogues: Reduced Toxicity of 5-Chlorinated 2',3'-Dideoxynucleosides

In view of the selective anti-HIV activity of 2',3'-dideoxy-3'-fluoro-5-chlorouridine (11), a series of eight 2',3'-dideoxy-5-chloropyrimidines were synthesized and evaluated for their inhibitory activity against human immunodeficiency virus type 1 (HIV-1) replication in MT-4 cells.A marked improvement in selectivity was noted for the 5-chlorouracil derivatives of 2,3-dideoxyribofuranose, 3-azido-2,3-dideoxyribofuranose, and 3-fluoro-2,3-dideoxyribofuranose, mainly due to decreased toxicity of the compounds for the host cells.While chlorination of 2',3'-dideoxycytidine remo ved the anti-HIV activity, introduction of chlorine at the C-5 position of 3'-fluoro-, 3'-azido- or 2',3'-didehydro-2',3'-dideoxycytidine led to reduced cytotoxicity with only slightly reduced anti-HIV activity.X-ray analysis showed compound 11 to have two molecules in the asymmetric unit with κ = -168.8(3) deg and -131.3(3) deg and P = 179(1) deg and 163(1) deg, respectively; thus revealing no close resemblance to 3'-azido-3'-deoxythymidine (AZT).