75797-17-0

Basic information

• Product Name: (1R,2S,3R,5R)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
• CAS NO: 75797-17-0
• Molecular Formula: C₁₁H₁₄ClN₅O₃
• Molecular Weight: 299.7136
• Mol File: 75797-17-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 647.8°C at 760 mmHg
• Flash Point: 345.6°C
• Density: 2.03g/cm³
• Vapor Pressure: 1.14E-17mmHg at 25°C
• Refractive Index: 1.887
• CAS DataBase Reference: (1R,2S,3R,5R)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,3R,5R)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol(75797-17-0)
• EPA Substance Registry System: (1R,2S,3R,5R)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol(75797-17-0)

Safety Data

• Hazardous Substances Data: 75797-17-0(Hazardous Substances Data)

Usage

Description

(1R,2S,3R,5R)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol is a complex organic compound characterized by a cyclopentane ring fused with a purine base. This molecule is adorned with a hydroxymethyl group and an amino group attached to the purine ring, and it also features a chlorine atom at the 6-position of the purine ring. The specific stereochemistry of (1R,2S,3R,5R) denotes the configuration of its chiral centers, which may influence its potential pharmaceutical or biological applications. Given the presence of the purine base, a component of nucleic acids with diverse biological functions, this compound holds promise for various applications in the medical and pharmaceutical fields.

Uses

Used in Pharmaceutical Development:
(1R,2S,3R,5R)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol is utilized as a key intermediate in the synthesis of pharmaceuticals targeting various diseases. Its unique structure, including the purine base and the chlorine substitution, may contribute to its activity against specific biological targets, making it a candidate for drug development.
Used in Biological Research:
In the field of biological research, this compound serves as a valuable tool for studying the interactions of purine-based molecules with enzymes, receptors, and other biomolecules. Its defined stereochemistry allows for precise investigations into the effects of chirality on biological activity and selectivity.
Used in Medicinal Chemistry:
(1R,2S,3R,5R)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol is employed in medicinal chemistry as a starting material for the design and synthesis of novel therapeutic agents. Its structural features can be further modified to optimize pharmacokinetic properties and enhance the compound's efficacy and safety.
Used in Drug Delivery Systems:
In drug delivery applications, this compound may be incorporated into formulations to improve the solubility, stability, or targeted delivery of therapeutic agents. Its hydrophilic and hydrophobic components can be leveraged to facilitate interactions with biological systems and enhance drug performance.
Used in Chemical Synthesis:
(1R,2S,3R,5R)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol is also used as a versatile building block in organic synthesis for the creation of a variety of chemical entities. Its functional groups and stereochemistry provide a foundation for the development of complex molecules with potential applications in various industries.

Upstream product

• 79200-57-0 (1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxylmethyl)-1-aminocyclopentan hydrochloride 
• 171887-03-9 N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide 
• 14036-06-7 diethoxymethyl acetate 
• 50619-39-1 (+/-)-2,5-diamino-4-N-<2α,3β-dihydroxy-4α-(hydroxymethyl)cyclopent-1α-yl>amino-6-chloropyrimidine 
• 91382-82-0 (+/-)-(1α,2β,3α,5α)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 108742-06-9 (+/-)-(1α,2β,3α,5α)-3-<<2-amino-6-chloro-5-<(4-chlorophenyl)azo>-4-pyrimidyl>amino>-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 108742-05-8 (+/-)-(1α,2β,3α,5α)-3-<(2-amino-6-chloro-4-pyrimidinyl)amino>-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 122-51-0 orthoformic acid triethyl ester 
• 108742-07-0 (+/-)-(1α,2β,3α,5α)-3-<(2,5-diamino-6-chloro-4-pyrimidyl)amino>-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 50619-39-1 (1S,2R,3S,5S)-3-(2,5-Diamino-6-chloro-pyrimidin-4-ylamino)-5-hydroxymethyl-cyclopentane-1,2-diol 
• 50796-89-9 (+/-)-(1α,2α,3α,5α)-3-<<2-amino-6-chloro-5-<(4-chlorophenyl)azo>-4-pyrimidinyl>amino>-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 125073-22-5 (+/-)-(1α,2α,3α,5α)-3-<(2-amino-6-chloro-4-pyrimidinyl)amino>-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 87419-91-8 (+/-)-(1α,2α,3α,5α)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 125073-24-7 (+/-)-(1α,2α,3α,5α)-3-<(2,5-diamino-6-chloro-4-pyrimidinyl)amino>-5-(hydroxymethyl)-1,2-cyclopentanediol 

Downstream Products

• 88801-89-2 (1α,2α,3β,5β)-(+/-)-3-<2-amino-6-(methylthio)-9H-purin-9-yl>-5-(hydroxymethyl)-1,2-cyclopentanediol 

Relevant articles and documents

RNAs Containing Carbocyclic Ribonucleotides

Toward the goal of evaluation of carbocyclic ribonucleoside-containing oligonucleotide therapeutics, we developed convenient, scalable syntheses of all four carbocyclic ribonucleotide phosphoramidites and the uridine solid-support building block. Crystall

Antiviral carbocyclic analogs of xylofuranosylpurines

Biologically-active (6-amino) purine nucleosides of the formula: STR1 are disclosed wherein X is CH or N, and R is selected from the group consisting of N(Y)(Z), SY, OY and halogen, wherein Y and Z are H, lower(alkyl), phenyl or mixtures thereof; and the pharmaceutically-acceptable salts thereof. The compounds exhibit antiviral and antitumor activity.

Synthesis and antiviral evaluation of carbocyclic analogues of ribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines

Carbocyclic analogues of ribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines were prepared from the 2-amino-6-chloropurine ribofuranoside analogue and the 2-amino-6-chloro-8-azapurine ribofuranoside analogue, respectively. Analogues of purine ribofuranosides with the chloro, amino, methylamino, or methylthio group at position 6, the thioguanosine analogue, and the previously reported guanosine analogue were evaluated in vitro against herpes simplex virus, type 1 (HSV-1). 8-Azapurine ribofuranoside analogues with the chloro, amino, or methylthio group at position 6 and the previously reported 8-azaguanosine analogue were also evaluated against HSV-1. The carbocyclic analogue of 2,6-diaminopurine ribofuranoside is highly active against HSV-1 and, also, against vaccinia virus. The 2-amino-6-chloropurine, 2-amino-6-(methylamino)purine, and the 2,6-diamino-8-azapurine derivatives also demonstrated significant activity against HSV-1.