112966-73-1

Basic information

• Product Name: 2-aMino-9-((1R,4S)-4-(hydroxyMethyl)cyclopent-2-enyl)-4,9-dihydro-1H-purin-6(5H)-one
• Synonyms: 2-aMino-9-((1R,4S)-4-(hydroxyMethyl)cyclopent-2-enyl)-4,9-dihydro-1H-purin-6(5H)-one;((1R,3S)-3-(6-Amino-9H-purin-9-yl)cyclopentyl)methanol
• CAS NO: 112966-73-1
• Molecular Formula: C₁₁H₁₅N₅O
• Molecular Weight: 249.2691
• Mol File: 112966-73-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-aMino-9-((1R,4S)-4-(hydroxyMethyl)cyclopent-2-enyl)-4,9-dihydro-1H-purin-6(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-aMino-9-((1R,4S)-4-(hydroxyMethyl)cyclopent-2-enyl)-4,9-dihydro-1H-purin-6(5H)-one(112966-73-1)
• EPA Substance Registry System: 2-aMino-9-((1R,4S)-4-(hydroxyMethyl)cyclopent-2-enyl)-4,9-dihydro-1H-purin-6(5H)-one(112966-73-1)

Safety Data

• Hazardous Substances Data: 112966-73-1(Hazardous Substances Data)

Usage

Function

Synthetic nucleoside analog used in HIV and AIDS treatment

Mechanism of Action

Inhibits reverse transcriptase enzyme crucial for HIV replication

Mode of Administration

Tablets and oral solutions

Usage

Typically used in combination with other antiretroviral medications

Efficacy

Reduces viral load, slows disease progression

Safety

Generally well-tolerated, but can cause serious allergic reactions

Administration

Under the supervision of a healthcare professional

Upstream product

• 1071906-28-9 9-[(1S,3R)-3-((tert-butyldiphenylsilyloxy)methyl)cyclopentyl]-9H-purin-6-amine 
• 178456-34-3 (1R,2R)-2-acetoxy-1-(acetoxymethyl)-3-cyclopentene 
• 66224-66-6 adenine 
• 918492-98-5 (1α,4α)-4-(6-Chloro-9H-purin-9-yl)-2-cyclopentenyl-carbinol 
• 168960-19-8 (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride 
• 151792-53-9 tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 168960-18-7 (1R,4S)-N-(tert-Butyloxycarbonyl)-1-amino-4-(hydroxymethyl)-2-cyclopentene 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 918492-97-4 (1S,cis)-4-[(5-amino-6-chloro-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol 
• 147332-45-4 (1α,4α)-4-(6-Amino-9H-purin-9-yl)-2-cyclopentenylcarbinol 

Downstream Products

• 515826-72-9 9-[3-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl]-8-phenyl-9H-purin-6-ylamine 

Relevant articles and documents

Synthesis of D- And L-carbocyclic nucleosides via rhodium-catalyzed asymmetric hydroacylation as the key step

(Chemical Equation Presented) D- and L-carbocyclic nucleosides were obtained by a new procedure involving an enantioselective rhodium/duphos- catalyzed hydroacylation reaction as the key step. The 3-hydroxymethyl- cyclopentanol intermediate was obtained by stereoselective reduction of ketone and by dynamic kinetic resolution (DKR).

Application of phosphoramidate ProTide technology significantly improves antiviral potency of carbocyclic adenosine derivatives

We report the application of phosphoramidate pronucleotide (ProTide) technology to the antiviral agent carbocyclic L-d4A (L-Cd4A). The phenyl methyl alaninyl parent ProTide of L-Cd4A was prepared by Grignard-mediated phosphorochloridate reaction and resulted in a compound with significantly improved anti-HIV (2600-fold) and HBV activity. We describe modifications of the aryl, ester, and amino acid regions of the ProTide and how these changes affect antiviral activity and metabolic stability. Separate and distinct SARs were noted for HIV and HBV. Additionally, ProTides were prepared from the D-nucleoside D-Cd4A and the dideoxy analogues L-CddA and D-CddA. These compounds showed more modest potency improvements over the parent drug. In conclusion, the ProTide approach is highly successful when applied to L-Cd4A with potency improvements in vitro as high as 9000-fold against HIV. With a view to preclinical candidate selection we carried out metabolic stability studies using cynomolgus monkey liver and intestinal S9 fractions.

Bisubstrate inhibitors for the enzyme catechol O-methyltransferase (COMT): Dramatic effects of ribose modifications on binding affinity and binding mode

Inhibition of the enzyme catechol O-methyltransferase (COMT) is of significant interest in the therapy of Parkinson's disease. Described herein are structural analogs of the potent bisubstrate inhibitor (-)-1 (IC50 = 9 nM; Table 1) for COMT, wi