107550-74-3

Basic information

• Product Name: [(2S,5R)-5-(2-amino-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol
• Synonyms: 2-furanmethanol, 5-(2-amino-9H-purin-9-yl)tetrahydro-, (2S,5R)-
• CAS NO: 107550-74-3
• Molecular Formula: C₁₀H₁₃N₅O₂
• Molecular Weight: 235.2425
• Mol File: 107550-74-3.mol

Chemical Properties

• Boiling Point: 570.8°C at 760 mmHg
• Flash Point: 299°C
• Density: 1.76g/cm³
• Vapor Pressure: 7.23E-14mmHg at 25°C
• Refractive Index: 1.822
• CAS DataBase Reference: [(2S,5R)-5-(2-amino-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [(2S,5R)-5-(2-amino-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol(107550-74-3)
• EPA Substance Registry System: [(2S,5R)-5-(2-amino-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol(107550-74-3)

Safety Data

• Hazardous Substances Data: 107550-74-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
[(2S,5R)-5-(2-amino-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol is used as a key compound for the development of drugs targeting purine receptors or adenosine signaling pathways. Its unique structure and chirality allow for the creation of novel therapeutic agents that can modulate these pathways, potentially leading to treatments for various diseases and conditions.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, [(2S,5R)-5-(2-amino-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol serves as a valuable starting material for the synthesis of new drug candidates. Its structural features can be exploited to design and develop innovative molecules with enhanced potency, selectivity, and pharmacokinetic properties, ultimately contributing to the advancement of drug discovery efforts.
Used in Drug Design and Development:
[(2S,5R)-5-(2-amino-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol is utilized as a building block in the design and development of new drugs. Its incorporation into drug molecules can potentially improve their interaction with biological targets, such as purine receptors, and enhance their overall therapeutic efficacy. [(2S,5R)-5-(2-amino-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol's unique properties make it a promising candidate for the development of novel therapeutic agents with improved pharmacological profiles.

Upstream product

• 452-06-2 9H-purin-2-amine 
• 5983-09-5 2',3'-Dideoxyuridine 

Downstream Products

• 122999-44-4 2,3-Didesoxy-β-D-glycero-pentofuranose 
• 452-06-2 9H-purin-2-amine 

Relevant articles and documents

Antiviral agents

Nucleoside compounds of the formula STR1 wherein: B is a purine or a pyrimidine; X and X' are H, OH or F, provided that at least one is H; Y and Y' are H, OH, OCH3 or F, provided that at least one is H; Y' and Z together form a cyclic phosphate ester, provided that Y is H; or Z is STR2 where n is zero, one, two or three; and Z' is N3 or OCH3 ; provided that when X' and Y' are OH and Z' is N3, B is not cytosine, and when X' and Y' are OH and Z' is OCH3, B is not uracil, adenine or cytosine; and the pharmaceutically acceptable esters, ethers and salts thereof, have been found to have potent antiviral activity with a high therapeutic ratio.

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.