128496-09-3

Basic information

• Product Name: 1-(2,3-dideoxy-2-fluoropentofuranosyl)-5-fluorocytosine
• Synonyms: 1-(2,3-dideoxy-2-fluoropentofuranosyl)-5-fluorocytosine;1-(2,3-Dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-5-fluorocytosine;4-Amino-1-(2-fluoro-2,3-dideoxy-β-D-threo-pentofuranosyl)-5-fluoro-2(1H)-pyrimidinone
• CAS NO: 128496-09-3
• Molecular Formula: C9H11F2N3O3
• Molecular Weight: 247.1987464
• Mol File: 128496-09-3.mol

Chemical Properties

• Boiling Point: 389.5°Cat760mmHg
• Flash Point: 189.4°C
• Appearance: /
• Density: 1.76g/cm³
• Vapor Pressure: 1.12E-07mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: 1-(2,3-dideoxy-2-fluoropentofuranosyl)-5-fluorocytosine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,3-dideoxy-2-fluoropentofuranosyl)-5-fluorocytosine(128496-09-3)
• EPA Substance Registry System: 1-(2,3-dideoxy-2-fluoropentofuranosyl)-5-fluorocytosine(128496-09-3)

Safety Data

• Hazardous Substances Data: 128496-09-3(Hazardous Substances Data)

Usage

Uses

Used in Antiviral Applications:
1-(2,3-dideoxy-2-fluoropentofuranosyl)-5-fluorocytosine is used as an antiviral agent for its potential to inhibit the replication of DNA and RNA viruses. It has shown promising results in preclinical studies, particularly against herpes simplex virus and human immunodeficiency virus (HIV). Further research and clinical trials are needed to fully evaluate its safety and efficacy for use in treating viral infections.
Used in Pharmaceutical Industry:
1-(2,3-dideoxy-2-fluoropentofuranosyl)-5-fluorocytosine is used as a potential candidate for the development of new antiviral drugs due to its unique structure and mechanism of action. Its effectiveness against various viruses makes it a valuable compound for pharmaceutical research and development, with the aim of creating new treatments for viral infections.

InChI:InChI=1/C9H11F2N3O3/c10-5-1-4(3-15)17-8(5)14-2-6(11)7(12)13-9(14)16/h2,4-5,8,15H,1,3H2,(H2,12,13,16)/t4-,5+,8+/m0/s1

Upstream product

• 128496-08-2 1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-5-fluorocytosine 
• 136228-19-8 5-O-benzoyl-2,3-dideoxy-2-fluoro-α-D-arabinofuranosyl bromide 
• 136228-16-5 5-O-Benzoyl-2,3-dideoxy-2-fluoro-1-O-methyl-β-D-threo-pentofuranose 
• 97614-44-3 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide 
• 128496-06-0 1-(5-O-benzoyl-2-deoxy-fluoro-β-D-arabinofuranosyl)-5-fluorocytosine 
• 128496-05-9 1-(3,5-O-dibenzoyl-2-fluoro-β-D-arabinofuranosyl)-5-fluorocytosine 
• 128496-07-1 1-<5-O-benzoyl-2-deoxy-fluoro-3-O--β-D-arabinofuranosyl>)-5-fluorocytosine 

Relevant articles and documents

2'-fluorofuranosyl derivatives and novel method of preparing 2'-fluoropyrimidine and 2'-fluoropurine nucleosides

A compound has the formula STR1 wherein R is selected from the group consisting of (C7 -C20)aroyl, (C6 -C20)aryl, aralkyl and alkylaryl, and (C1 -C10)alkyl-di(C6 -C20)aryl Si, R' is selected from the group consisting of (C1 -C10)alkyl, (C7 -C20)aroyl and (C2 -C12)acyl, all of which may be further substituted with O, S, N or alkyl, and R'" is selected from the group consisting of halogen, (C1 -C10)alkoxy, (C1 -C10)acyloxy, O-methane-sulfonyl and O-p-toluenesulfonyl. A composition of matter comprises 0.001 to 99.999 wt % of the above compound.

Chemistry and anti-HIV properties of 2'-fluoro-2',3'- dideoxyarabinofuranosylpyrimidines

The synthesis, chemistry, biochemistry, and anti-HIV activity of a series of 1-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)pyrimidines have been studied in an attempt to find useful anti-AIDS drugs. Synthesis is carried out via a 2,3-dideoxyribose intermediate which facilitates the preparation of analogues by removing the sugar 3'-hydroxyl group prior to, rather than after, condensation with a uracil or cytosine aglycon. The 2'-F-dd-uridine analogues 7a-d (with H, F, Cl, and CH3 substitution in the 5-position) as well as the 4-deoxy compound (12b) are nonprotective to ATH8 or CEM cells infected with HIV-1. In the corresponding cytidine series, the 5-chloro analogue (11) is inactive. However, 2'-fluoro-2',3'- dideoxyarabinosylcytosine, 10a, and its 5-fluoro analogue, 10b, are both active. While neither compound is as potent as ddC or 5-F-ddC (2b), 10b gives complete protection against the cytopathic effects of HIV in both host cell lines. 2'-Fluoro substitution confers increased chemical and enzymatic stability on dideoxynucleosides. Even though dideoxy pyrimidine nucleosides are inherently more stable than the corresponding purine analogues toward acid-catalyzed cleavage of the glycosidic bond, 2'-fluoro substitution (10a) still increases stabilization relative to ddC (2b). No detectable deamination by partially purified cytidine deaminase is observed with the 2'-fluoro compounds 10a, 10b, or 11 under conditions which rapidly deaminate cytidine. A small amount of 2'-F-dd-ara-U (7a) is formed from 10a in monkey plasma after >24 h of exposure. The octanol-water partition coefficients for the dideoxynucleosides in this study indicate their hydrophilic character, with log P values varying from -0.28 to -1.18.

Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1)

A range of 2'-fluoro and 2',3'-difluoro analogues of pyrimidine deoxyribonucleosides have been synthesized and evaluaed against human immunodeficiency virus (HIV-1) in a human lymphoblastoid cell line. Among these compounds, 1-(2,3-dideoxy-2-fluoro-β-D-threopentofuranosyl)cytosine (12), 2',3'-didehydro-2',3'-dideoxy-2'-fluorocytidine (35), 1-(2,3-dideoxy-2,3-difluoro-β-D-arabinofuranosyl)cytosine (41), and 3'-deoxy-2',3'-didehydro-2'-fluorothymidine (45) were found to have significant antiviral activity, with IC50 values of 0.65, 10, 10, and 100 μM, respectively. The structure-activity relationships are discussed.