145913-80-0

Usage

Uses

Used in Pharmaceutical Industry:
[(2R,5S)-5-(6-amino-2-fluoro-9H-purin-9-yl)-1,3-oxathiolan-2-yl]methanol is used as a pharmaceutical compound for its potential role in the development of new drugs. The presence of a purine derivative suggests that it may have applications in treating various diseases, particularly those related to nucleic acid metabolism or purinergic signaling pathways.
Used in Research and Development:
In the field of chemical research and development, [(2R,5S)-5-(6-amino-2-fluoro-9H-purin-9-yl)-1,3-oxathiolan-2-yl]methanol serves as a valuable compound for studying the effects of stereochemistry on biological activity. Its unique structure, including the fluorine atom and the thiol group, makes it an interesting subject for exploring novel chemical reactions and potential applications in medicinal chemistry.
Used in Drug Design and Synthesis:
[(2R,5S)-5-(6-amino-2-fluoro-9H-purin-9-yl)-1,3-oxathiolan-2-yl]methanol is utilized in drug design and synthesis as a building block or a template for creating new pharmaceutical agents. Its complex molecular structure, with the potential for multiple points of modification, allows for the development of a variety of drug candidates with tailored properties and therapeutic effects.

Upstream product

• 149819-68-1 (-)(2S,5S)-2-fluoro-6-amino-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine 
• 149819-67-0 (-)(2S,5R)-2-fluoro-6-amino-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine 
• 149712-96-9 2-fluoro-6-chloropurine 
• 1651-29-2 6-chloro-2-fluoropurine 
• 145986-40-9 (+)-(2R,5R)-2-fluoro-6-amino-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine 
• 145913-78-6 (+)-(2R,5S)-2-fluoro-6-amino-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine 

Relevant academic research and scientific papers

Structure-Activity Relationships of β-D-(2S,5R)- and α-D-(2S,5S)-1,3-oxathiolanyl Nucleosides as Potential Anti-HIV Agents

The β-D-(2S,5R)- and α-D-(2S,5S)-1,3-oxathiolanylpyrimidine and -purine nucleosides with natural nucleoside configuration were synthesized and evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells.The key intermediate 14, which was uti

Asymmetric Synthesis and Biological Evaluation of β-L-(2R,5S)- and α-L-(2R,5R)-1,3-Oxathiolane-Pyrimidine and -Purine Nucleosides as Potential Anti-HIV Agents

In order to study the structure-acivity relationships of L-oxathiolanyl nucleosides as potential anti-HIV agents, a series of enantiomerically pure L-oxathiolanyl pyrimidine and purine nucleosides were synthesized and evaluated for anti-HIV-1 activity in human peripheral blood mononuclear (PBM) cells.The key intermediate 8 was synthesized starting from L-gulose via 1,6-thiaanhydro-L-gulopyranose.The acetate 8 was condensed with thymine, 5-substituted uracils and cytosines, 6-chloropurine, and 6-chloro-2-fluoropurine to give pyrimidine and purine nucleosides.Upon evaluation of these final nucleosides, the 5-fluorocytosine derivative 51 was found to be the most potent compound among those tested.In the case of 5-substituted cytosine analogues, the antiviral potency was found to be in the following decreasing order: cytosine (β-isomer) > 5-iodocytosine (β-isomer) > 5-fluorocytosine (α-isomer) > 5-methylcytosine (α-isomer) > 5-methylcytosine (β-isomer) > 5-bromocytosine (β-isomer) > 5-chlorocytosine (β-isomer).Among the thymine, uracil, and 5-substituted uracil derivatives, thymine (α-isomer) and uracil (β-isomer) derivatives exhibited moderate anti-HIV activity.In the purine series, the antiviral potency is found to be in the following decreasing order: adenine (β-isomer) > 6-chloropurine (β-isomer) > 6-chloropurine (α-isomer) > 2-NH2-6-Cl-purine (β-isomer) > guanine (β-isomer) > N6-methyladenine (α-isomer) > N6-methyladenine (β-isomer).The cytotoxicity was also determined in human PBM cells as well as Vero cells.None of the synthesized nucleosides was toxic up to 100 μ in PBM cells.