51246-79-8

Usage

Uses

Used in Pharmaceutical Industry:
2',3'-dideoxy-3'-fluorocytidine is used as an antiviral agent for the treatment of HIV infection. It is valued for its ability to inhibit the replication of the virus, thereby slowing the progression of the disease and providing a potential therapeutic option for patients.
Used in Clinical Research:
In the field of clinical research, 2',3'-dideoxy-3'-fluorocytidine is used as a subject of investigation for its potential applications in treating HIV and possibly other viral infections. Ongoing studies aim to understand its full spectrum of effects, optimize its use, and mitigate the side effects associated with its administration.
Used in Drug Development:
2',3'-dideoxy-3'-fluorocytidine serves as a key compound in the development of new antiviral drugs. Researchers are exploring ways to improve its safety profile and effectiveness, with the goal of creating more potent and safer treatments for HIV and related conditions.

Upstream product

• 585540-22-3 2'-chloro-2',3'-dideoxy-3'-fluorocytidine 
• 585540-17-6 1-(5-O-benzoyl-2-chloro-2,3-dideoxy-3-fluoro-β-D-ribofuranosyl)-N⁴-benzoylcytosine 
• 133776-09-7 methyl 5-O-benzoyl-2-O-tosyl-3-fluoro-3-deoxy-β-D-arabinofuranoside 
• 126716-24-3 methyl 5-O-benzyl-2-O-tosyl-3-fluoro-3-deoxy-β-D-arabino-furanoside 
• 585540-10-9 ((2R,3R,4S,5R)-4-Chloro-3-fluoro-5-methoxy-tetrahydro-furan-2-yl)-methanol 
• 585540-09-6 methyl 5-O-benzyl-2-chloro-2,3-dideoxy-3-fluoro-β-D-ribofuranoside 
• 585540-11-0 methyl 5-O-benzoyl-2-chloro-2,3-dideoxy-3-fluoro-β-D-ribofuranoside 
• 108895-51-8 N⁴-benzoyl-2'-deoxy-3'-O-mesyl-5'-O-tritylcytidine 
• 108895-50-7 1-(5-O-trityl-2-deoxy-β-D-threo-pentofuranosyl)cytosine 

Downstream Products

• 141018-21-5 N⁴-<(diisopropylamino)methylene>-3;-fluoro-2',3'-dideoxycytidine 

Relevant academic research and scientific papers

2'-chloro-2',3'-dideoxy-3'-fluoro-d-ribonucleosides: synthesis, stereospecificity, some chemical transformations, and conformational analysis.

The synthesis of methyl 5-O-benzoyl-2-chloro-2,3-dideoxy-3-fluoro-beta-d-ribofuranoside (5) and its use as a glycosylating agent for persilylated thymine, N(6)-benzoyladenine, and N(4)-benzoylcytosine are described (Scheme 1). The 2'-chloro-2',3'-dideoxy-3'-fluoro-d-ribonucleosides 10-12 synthesized were transformed to 2',3'-dideoxy-3'-fluoro-alpha- and -beta-d-erythro-pentofuranoside nucleosides of thymine (13a,b), adenine (14a,b), and cytidine (15a,b) by treatment with tributyltin hydride in the presence of alpha,alpha'-azobisisobutyronitrile (Scheme 2). Treatment of 2'-chloro-2',3'-dideoxy-3'-fluoro-d-ribonucleosides with 1 M MeONa/MeOH under reflux for 1-5 h afforded 2',3'-didehydro-2',3'-dideoxy-2'-chloro-d-pentofuranosyl nucleosides as the principal products (47-81%) of the reaction, along with recovered starting nucleoside (11-33%) (Scheme 3). Easy HF elimination was also observed in the case of the 2'-azido-2',3'-dideoxy-3'-fluoro-beta-d-ribofuranosides of thymine (17) and adenine (20) (Scheme 3). The role of conformational peculiarities of 2'-chloro-2',3'-dideoxy-3'-fluoro-d-ribonucleosides as well as of 17 and 20 in the observed exclusive elimination of HF is discussed. The conformational analysis of a rather broad palette of 2,3-dideoxy-3-fluoro-2-(X-substituted)-d-ribofuranosides was performed with the aid of the PSEUROT (version 6.3) program, using (i) the recently reparametrized Karplus-type relation (Chattopadhyaya and co-workers. J. Org. Chem. 1998, 63, 4967) and (ii) empirical bond angle correction terms suggested by us. The predictive power of the Brunck and Weinhold model (J. Am. Chem. Soc. 1979, 101, 1700) of the gauche effect between atoms and groups as a conformational driving force acting upon the pentofuranose ring is explored. Their model invokes maximum antiperiplanar sigma sigma stabilization when the donating bond is the least polar one and the acceptor orbital is at the most polarized bond and is found at least as satisfactory, and in various specific cases more so than, as rationalizations on the basis of the preference of the gauche vs the trans conformation of two vicinal electronegative substituents (Wolfe. Acc. Chem. Res. 1972, 5, 102).

3'-Substituted 2',3'-Dideoxynucleoside Analogues as Potential Anti-HIV (HTLV-III/LAV) Agents

A series of 2',3'-unsaturated and 3'-substituted 2',3'-dideoxynucleoside analogues of purines and pyrimidines have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV).The 2',3'-unsaturated analogues of 2',3'-dideoxycytidine (ddeCyd) and 2',3'-dideoxythymidine (ddeThd), 3'-azido-2',3'-dideoxythymidine (AzddThd), 3'-fluoro-2',3'-dideoxythymidine, 2',3'-dideoxycytidine (ddCyd), and 2',3'-dideoxyadenosine (ddAdo) emerged as the most potent inhibitors of HIV-induced cytopathogenicity in the human T lymphocyte cell lines ATH8 and MT4.In ATH8 cells ddCyd, ddeCyd, and ddAdo had the highest therapeutic index whereas in MT4 cells AzddThd, ddThd, ddCyd, and ddAdo were the most selective.Derivatives from ddThd in which the substituent group was linked to the 3'-carbon atom via a thio, sulfonyl, or oxygen bridge were far less inhibitory to HIV than was AzddThd.