75797-17-0

Usage

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, (1R,2S,3R,5R)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol 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, (1R,2S,3R,5R)-3-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol 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

• 125073-24-7 (+/-)-(1α,2α,3α,5α)-3-<(2,5-diamino-6-chloro-4-pyrimidinyl)amino>-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 122-51-0 orthoformic acid triethyl ester 
• 14036-06-7 diethoxymethyl acetate 
• 50619-39-1 (+/-)-2,5-diamino-4-N-<2α,3β-dihydroxy-4α-(hydroxymethyl)cyclopent-1α-yl>amino-6-chloropyrimidine 
• 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 
• 75829-33-3 (+/-)-(1α,2β,3β,5β)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol 
• 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 
• 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 

Downstream Products

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

Relevant academic research and scientific papers

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

Synthesis and Biological Evaluation of Carbocyclic Analogues of Lyxofuranosides of 2-Amino-6-substituted-purines and 2-Amino-6-substituted-8-azapurines

Carbocyclic analogues of lyxofuranosides of 2-amino-6-substituted-purines and 2-amino-6-substituted-8-azapurines were synthesized from (+/-)-(1α,2α,3α,5α)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol (2) and 2-amino-4,6-dichloropyrimidine (3).The 2-amin

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 activity of carbocyclic analogues of xylofuranosides of 2-amino-6-substituted-purines and 2-amino-6-substituted-8-azapurines

(±)-(1α,2β,3α,5α)-3-[(2,5-Diamino-6-chloro-4-pyrimidinyl)amino] -5-(hydroxmethyl)-1,2-cyclopentanediol (7) was synthesized from 2-amino-4,6-dichloropyrimidine and the carbocyclic xylofuranosylamine (±)-(1α,2β,3α,5α)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol (2) by subsequent preparation of the 5-[(4-chlorophenyl)azo] derivative of the resulting pyrimidine and reduction of the azo moiety with zinc and acetic acid. The carbocyclic analogue of 2-amino-4-chloropurine xylofuranoside (8) and the corresponding 8-azapurine 11 were prepared from 7. The carbocyclic analogues xylofuranosylguanine (9), xylofuranosyl-2,6-diaminopurine (10), xylofuranosyl-8-azaguanine (13), and xylofuranosyl-8-aza-2,6-diaminopurine (14) were prepared from 8 and 11. Compounds 9 and 13 were active against herpes simplex virus (types 1 and 2), with 9 being the more potent against both viruses. Analogues 9 also exhibited potent activity against human cytomegalovirus and varicella-zoster virus.

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.