23205-67-6

Usage

Uses

Used in Pharmaceutical Industry:
8-FLUOROADENOSINE is used as an active pharmaceutical ingredient for the development of drugs targeting specific diseases. Its unique structure allows it to modulate biological processes and potentially offer therapeutic benefits.
Used in Research and Development:
8-FLUOROADENOSINE serves as a valuable tool in the field of research, particularly in the study of nucleophilic substitutions. The intermediate generation of 8-fluoroadenosines can help increase the reaction rates of these substitutions, providing insights into the underlying mechanisms and potentially leading to the development of new chemical processes or compounds.
Used in Drug Synthesis:
The first non-enzymatic synthesis of 8-FLUOROADENOSINE has been described, which opens up possibilities for its large-scale production and application in various industries. This synthesis method can be further optimized and adapted for the creation of other related compounds with potential applications in medicine and other fields.

InChI:InChI=1/C10H12FN5O4/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,13,14)

Upstream product

• 23205-66-5 O^2'_,O3'_,O5'5'-triacetyl-8-fluoro-adenosine 
• 938052-99-4 8-fluoro-2',3'-O-(1-methylethylidene)-5'-O-(tetrahydro-2H-pyran-2-yl)adenosine 
• 64-19-7 acetic acid 
• 64-18-6 formic acid 
• 938053-00-0 8-fluoro-2',3'-O-(1-methylethylidene)adenosine 
• 2946-39-6 8-bromoadenosine 
• 13089-45-7 8-bromo-2',3'-O-isopropylene adenosine 
• 58-61-7 adenosine 
• 104354-34-9 8-bromo-2',3'-O-(1-methylethylidene)-5'-O-(tetrahydro-2H-pyran-2-yl)adenosine 

Relevant academic research and scientific papers

The Elusive 8-Fluoroadenosine

The synthesis of 8-fluoroadenosine has been accomplished for the first time.The kinetics of deamination of 8-fluoroadenosine with the enzyme adenosine deaminase has also been measured. - Keywords: Enzymes and Enzyme reactions; Fluorine and compounds; Nucleosides; Purines

The elusive 8-fluoroadenosine: a simple non-enzymatic synthesis and characterization

The only successful synthesis of 8-fluoroadenosine reported until now relied on an enzymatic removal of the acetate protecting groups using thermally resistant hydrolases. In the present communication we describe the first non-enzymatic synthesis of 8-fluoroadenosine. According to this, the C8-fluorine atom was introduced in a halogen-exchange process performed at elevated temperature. The chief obstacle in the synthesis of 8-fluoroadenosine, the removal of the protecting groups in the presence of the labile C8-F bond, was addressed by judicious choice of acid-labile protecting groups. Their deprotection in the presence of C8-F is described. Using this newly developed procedure, significant quantities of 8-fluoroadenosine were synthesized and, for the first time, its physicochemical properties including pH-dependent stability, examined in detail. The intermediate generation of 8-fluoroadenosines as a tool to increase the reaction rates of nucleophilic substitutions was briefly examined and successfully demonstrated with the example of 8-cyanoadenosine. The presented procedure is applicable to the synthesis of various adenosine analogs with potential pharmacological significance.