134444-47-6

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-2'-deoxy-2'-fluoro-D-adenosine is used as an anticancer agent for its ability to resist degradation by adenosine deaminase, leading to increased stability and efficacy in inhibiting cell proliferation and inducing apoptosis in cancer cells.
Used in Cancer Research:
2-Amino-2'-deoxy-2'-fluoro-D-adenosine is used as a research tool for studying the mechanisms of action of adenosine analogues in cancer cells, providing insights into potential therapeutic strategies and drug development.
Used in Drug Development:
2-Amino-2'-deoxy-2'-fluoro-D-adenosine is used as a lead compound in the development of novel anticancer drugs, leveraging its pharmacological efficiency and stability to create more effective treatments for various types of cancer.

Upstream product

• 1904-98-9 2,6-diaminopurine 
• 56287-17-3 2'-deoxy-2'-fluorouridine 
• 10212-20-1 2'-deoxy-2'-fluorocytidine 
• 156357-16-3 2,6-dichloro-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)purine 
• 52826-86-5 1,6-diaminopurine 
• 5451-40-1 2,6-dichloro-7H-purine 
• 156357-13-0 2,6-diazido-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)purine 
• 149623-91-6 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranoside 
• 156357-14-1 2,6-diamino-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)purine 

Downstream Products

• 78842-13-4 2'-deoxy-2'-fluoroguanosine 
• 147048-53-1 2'-Deoxy-2,2'-difluoro-adenosine 
• 1431557-60-6 2-amino-2’-fluoro-2’-deoxyadenosine-5’-O-naphthyl(benzoxy-L-alaninyl)phosphate 
• 1431557-61-7 2-amino-2’-fluoro-2’-deoxyadenosine-5’-O-naphthyl(cyclohexoxy-L-alaninyl)phosphate 
• 1431557-63-9 2-amino-2’-fluoro-2’-deoxyadenosine-5’-O-phenyl(benzoxy-L-alaninyl)phosphate 
• 1431557-64-0 2-amino-2’-fluoro-2’-deoxyadenosine-5’-O-phenyl(cyclohexoxy-L-alaninyl)phosphate 
• 1431557-65-1 2-amino-2’-fluoro-2’-deoxyadenosine-5’-O-phenyl(ethoxy-L-alaninyl)phosphate 

Relevant academic research and scientific papers

Chemical and enzymatic synthesis and antiviral properties of 2'-deoxy- 2'-fluoroguanosine

Chemical and enzymatic methods were employed for the synthesis of the title compound, 2'F-Guo 7. High antiviral activity of 2'F-Guo was established in chick embryo cells infected with influenza virus FPV/Rostock/34 (H7N1) and herpes simplex virus (HSV) type I (1C strain).

Enzymatic Synthesis of Therapeutic Nucleosides using a Highly Versatile Purine Nucleoside 2’-DeoxyribosylTransferase from Trypanosoma brucei

The use of enzymes for the synthesis of nucleoside analogues offers several advantages over multistep chemical methods, including chemo-, regio- and stereoselectivity as well as milder reaction conditions. Herein, the production, characterization and utilization of a purine nucleoside 2’-deoxyribosyltransferase (PDT) from Trypanosoma brucei are reported. TbPDT is a dimer which displays not only excellent activity and stability over a broad range of temperatures (50–70 °C), pH (4–7) and ionic strength (0–500 mM NaCl) but also an unusual high stability under alkaline conditions (pH 8–10). TbPDT is shown to be proficient in the biosynthesis of numerous therapeutic nucleosides, including didanosine, vidarabine, cladribine, fludarabine and nelarabine. The structure-guided replacement of Val11 with either Ala or Ser resulted in variants with 2.8-fold greater activity. TbPDT was also covalently immobilized on glutaraldehyde-activated magnetic microspheres. MTbPDT3 was selected as the best derivative (4200 IU/g, activity recovery of 22 %), and could be easily recaptured and recycled for >25 reactions with negligible loss of activity. Finally, MTbPDT3 was successfully employed in the expedient synthesis of several nucleoside analogues. Taken together, our results support the notion that TbPDT has good potential as an industrial biocatalyst for the synthesis of a wide range of therapeutic nucleosides through an efficient and environmentally friendly methodology.

Anti-HCV nucleoside derivatives

The present invention comprises nucleoside derivatives for use in the treatment or prophylaxis of hepatitis C virus infections. In particular, the present invention discloses the novel use of known 2'-deoxy-2'-fluoro nucleoside derivatives as inhibitors of hepatitis C virus (HCV) RNA replication and pharmaceutical compositions of such compounds. The compounds of this invention have potential use as therapeutic agents for the treatment of HCV infections.

Method for the treatment of protoza infections with 21 -deoxy-21 -fluoropurine nucleosides

A method for treating two specific protozoal infections, Trichomonas vaginalis and Giardia lamblia, comprising the administration to a mammal in need thereof one of the following purine nucleosides: 2,6-diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine 2-amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine 2-amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-6-methoxy-9H-purine.

Synthesis and biologic activity of purine 2'-deoxy-2'-fluoro- ribonucleosides

The synthesis of 3,5-di-O-benzoyl-2-deoxy-2-fluoro-D-ribofuranosyl bromide (8) and its reaction with 2,6-dichloropurine by fusion and with mercuric cyanide catalysis is described. The resulting 2,6-dichloro-9-(3,5-di-O- benzoyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)purine (13) was converted to the 2-fluoroadenine (16), the 2-chloroadenine (17), 2,6-diaminopurine (12), and guanine (14) nucleosides by standard procedures. These nucleosides were cytotoxic to a number of cell lines in culture. The 2-haloadenine nucleosides 16 and 17 gave modest increases in lifespan when tested against the P388 leukemia in mice.

Purine 2'-deoxy-2'-fluororibosides as antiinfluenza virus agents

Twenty purine 2'-deoxy-2'-fluororibosides were synthesized by enzymic pentosyl transfer from 2'-deoxy-2'-fluorouridine. Each nucleoside analogue was assayed for cytotoxicity in uninfected Madin-Darby canine kidney cells and for their ability to suppress influenza A virus infections in these cells. The most potent antivirial activity was observed with analogues having an amino group in the 2-position of the purine moiety. All 2-unsubstituted analogues were less potent than their 2-amino counterparts. Furthermore, 2- methyl, 2-methoxy, or 2-fluoro substitution obliterated antivirial activity. The most cytotoxic member of the series was the 2-fluoro-6-amino analogue (IC50 = 120 μM). 2'-Deoxy-2'-fluoroguanosine and those congeners readily converted to it by adenosine deaminase showed the most potent antivirial activity (IC50 = 15-23 μM). Little cytotoxicity was observed with this subgroup of analogues which renders them worthy of further investigation as potential antiinfluenza agents.

Antiviral compounds

The present invention relates to 2?-fluoro substituted purine nucleosides and their use in medical therapy, particularly for the treatment of infectious diseases including influenza virus and respiratory syncytial virus infections, to methods for their preparation and to compositions containing them.