132194-25-3

Basic information

• Product Name: (2S)-5α-(6-Bromo-9H-purine-9-yl)tetrahydro-2α-furanmethanol
• Synonyms: (2S)-5α-(6-Bromo-9H-purine-9-yl)tetrahydro-2α-furanmethanol;6-Bromo-9-(2,3-dideoxy-β-D-ribofuranosyl)-9H-purine
• CAS NO: 132194-25-3
• Molecular Formula: C₁₀H₁₁BrN₄O₂
• Molecular Weight: 299.12394
• Mol File: 132194-25-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 505°Cat760mmHg
• Flash Point: 259.2°C
• Appearance: /
• Density: 2g/cm³
• Vapor Pressure: 5.11E-11mmHg at 25°C
• Refractive Index: 1.8
• CAS DataBase Reference: (2S)-5α-(6-Bromo-9H-purine-9-yl)tetrahydro-2α-furanmethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-5α-(6-Bromo-9H-purine-9-yl)tetrahydro-2α-furanmethanol(132194-25-3)
• EPA Substance Registry System: (2S)-5α-(6-Bromo-9H-purine-9-yl)tetrahydro-2α-furanmethanol(132194-25-3)

Safety Data

• Hazardous Substances Data: 132194-25-3(Hazardous Substances Data)

Usage

General Description

(2S)-5α-(6-Bromo-9H-purine-9-yl)tetrahydro-2α-furanmethanol is a chemical compound with the molecular formula C15H18BrN5O2. It is a derivative of the purine nucleoside adenosine, with a bromine substitution at the 6th position of the purine ring. (2S)-5α-(6-Bromo-9H-purine-9-yl)tetrahydro-2α-furanmethanol is a potent adenosine A1 receptor agonist, meaning it can selectively bind to and activate the A1 receptors in the body. It has been studied for its potential pharmacological effects, including its ability to reduce cardiac ischemia, improve renal function, and protect against neuronal damage. Its unique structure and pharmacological activity make it a promising candidate for further research and potential therapeutic applications.

InChI:InChI=1/C10H11BrN4O2/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(3-16)17-7/h4-7,16H,1-3H2/t6-,7+/m0/s1

Upstream product

• 767-69-1 6-bromopurine 
• 5983-09-5 2',3'-Dideoxyuridine 

Relevant articles and documents

Escherichia coli mediated biosynthesis and in vitro anti-HIV activity of lipophilic 6-halo-2',3'-dideoxypurine nucleosides

A series of 6-substituted 2',3'-dideoxypurine ribofuranosides (ddP) was enzymatically synthesized with live E. coli in an effort to enhance the lipophilicity of this class of anti-human immunodeficiency virus (HIV) compounds and thereby facilitate drug delivery into the central nervous system. All 6-halo-substituted ddPs were substantially more lipophilic, as defined by their octanol-water partition coefficient (P), than their nonhalogenated congeners 2',3'-dideoxyinosine (ddI) or 2',3'-dideoxyguanosine (ddG). For this class of compounds, log P's ranged from +0.5 to -1.2 in the following order: 6-iodo, 2-amino-6-iodo > 6-bromo, 2-amino-6-bromo > 6-chloro, 2-amino-6-chloro > 6-fluoro, 2-amino-6-fluoro >> ddG > ddI. These compounds were evaluated in vitro for ability to suppress the infectivity, replication, and cytopathic effect of HIV. 2-Amino-6-fluoro-, 2-amino-6-chloro-, and 6-fluoro-ddP exhibited a potent activity against HIV comparable to that of ddI or ddG and completely blocked the infectivity of HIV without affecting the growth of target cells. The comparative order of in vitro anti-HIV activity was 2-amino-6-fluoro, 2-amino-6-chloro, 6-fluoro > 2-amino-6-bromo > 2-amino-6-iodo, 6-chloro > 6-bromo > 6-iodo. These compounds also exhibited potent in vitro activity against HIV-2 and 3'-azido-3'-deoxythymidine-resistant HIV-1 variants. All 2-amino-6-halo-ddPs and 6-halo-ddPs were substrates for adenosine deaminase (ADA) and were converted to ddG or ddI, respectively. In the presence of the potent ADA inhibitor 2'-deoxycoformycin, 6-halo-substituted ddPs failed to exert an in vitro antiretroviral effect. These dideoxypurine nucleoside analogues represent a new class of lipophilic prodrugs of ddG and ddI that possess the potential for more effective therapy of HIV-induced neurologic disorders.