145986-43-2

Basic information

• Product Name: [(2R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-1,3-oxathiolan-2-yl]methanol
• Synonyms: 1,3-Oxathiolane-2-methanol, 5-(2-amino-6-chloro-9H-purin-9-yl)-, (2R-trans)-
• CAS NO: 145986-43-2
• Molecular Formula: C₉H₁₀ClN₅O₂S
• Molecular Weight: 287.726
• Mol File: 145986-43-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 660.4°C at 760 mmHg
• Flash Point: 353.2°C
• Density: 2.03g/cm³
• Vapor Pressure: 2.42E-18mmHg at 25°C
• Refractive Index: 1.906
• CAS DataBase Reference: [(2R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-1,3-oxathiolan-2-yl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [(2R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-1,3-oxathiolan-2-yl]methanol(145986-43-2)
• EPA Substance Registry System: [(2R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-1,3-oxathiolan-2-yl]methanol(145986-43-2)

Safety Data

• Hazardous Substances Data: 145986-43-2(Hazardous Substances Data)

Usage

General Description

[(2R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-1,3-oxathiolan-2-yl]methanol is a chemical compound with a complex molecular structure. It contains a purine ring, which is a heterocyclic aromatic organic compound, as well as an oxathiolane ring and a methanol group. The compound also contains an amino group and a chlorine atom. This chemical is likely to have biological activity due to its complex structure, which may enable it to interact with biological molecules such as proteins and nucleic acids. It may also have potential applications in medicinal chemistry or as a research tool in biochemistry.

Upstream product

• 149712-96-9 2-fluoro-6-chloropurine 
• 1651-29-2 6-chloro-2-fluoropurine 
• 145986-41-0 (-)-(2R,5R)-2-amino-6-chloro-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>purine 

Relevant articles and documents

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.