158799-91-8

Basic information

• Product Name: 2-Cyclopentene-1-methanol, 4-(6-chloro-9H-purin-9-yl)-, (1R,4S)-
• CAS NO: 158799-91-8
• Molecular Formula: C11H11ClN4O
• Molecular Weight: 250.688
• Mol File: 158799-91-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-Cyclopentene-1-methanol, 4-(6-chloro-9H-purin-9-yl)-, (1R,4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclopentene-1-methanol, 4-(6-chloro-9H-purin-9-yl)-, (1R,4S)-(158799-91-8)
• EPA Substance Registry System: 2-Cyclopentene-1-methanol, 4-(6-chloro-9H-purin-9-yl)-, (1R,4S)-(158799-91-8)

Safety Data

• Hazardous Substances Data: 158799-91-8(Hazardous Substances Data)

Upstream product

• 130931-83-8 (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one 
• 153011-43-9 (1S,cis)-tert-butyl N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]carbamate 
• 168960-19-8 (1S,4R)-1-amino-4-hydroxymethyl-2-cyclopentene hydrochloride 
• 287473-95-4 (1R,cis)-4-[(5-Amino-6-chloro-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol 
• 122-51-0 orthoformic acid triethyl ester 
• 200002-41-1 (-)-[(1R,4S)-tert-butyl 3-oxo-2-azabicyclo(2.2.1)hept-5-ene-2-carboxylate] 

Downstream Products

• 220285-03-0 [(1R,3S)-3-(6-amino-9H-purin-9-yl)cyclopentyl]methanol 
• 287477-82-1 2-{[4-(6-amino-purin-9-yl)-cyclopent-2-enylmethoxy]-phenoxy-phosphorylamino}-3-(4-tert-butoxy-phenyl)-propionic acid methyl ester 

Relevant articles and documents

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.