90597-20-9

Basic information

• Product Name: cyclopentenyluracil
• Synonyms: cyclopentenyluracil
• CAS NO: 90597-20-9
• Molecular Formula: C10H12N2O5
• Molecular Weight: 240.2127
• Mol File: 90597-20-9.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.644g/cm³
• Refractive Index: 1.682
• PKA: 9.60±0.10(Predicted)
• CAS DataBase Reference: cyclopentenyluracil(CAS DataBase Reference)
• NIST Chemistry Reference: cyclopentenyluracil(90597-20-9)
• EPA Substance Registry System: cyclopentenyluracil(90597-20-9)

Safety Data

• Hazardous Substances Data: 90597-20-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H12N2O5/c13-4-5-3-6(9(16)8(5)15)12-2-1-7(14)11-10(12)17/h1-3,6,8-9,13,15-16H,4H2,(H,11,14,17)/t6-,8-,9+/m1/s1

Upstream product

• 89291-76-9 (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol 
• 100806-47-1 (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol p-toluenesulfonate 
• 90597-18-5 (1R,2S,3R)-1--2,3-isopropylidenedioxy-4-methoxymethyloxymethyl-4-cyclopentene 
• 377748-89-5 (1'R,2'S,3'R)-N³-benzoyl-1-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]uracil 
• 377748-59-9 (1S,2R,3R)-1-acetoxy-2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten 
• 377748-57-7 (1R,2S,3S)-1-acetoxy-2,3-(isopropylidenedioxy)-1-(tert-butoxymethyl)-4-cyclopenten 
• 377748-56-6 (1R,2S,3S)-1-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)-4-cyclopenten-1-ol 
• 104010-72-2 (3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one 
• 377748-92-0 (1'R,2'S,3'R)-1-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]uracil 
• 90597-19-6 1-<(1R,2S,3R)-2,3-isopropylidenedioxy-4-methoxymethyloxymethyl-4-cyclopenten-1-yl>-2,4-(1H,3H)-pyrimidinedione 
• 92642-69-8 (1R,4R,5S)-(-)-1-<3-<(benzyloxy)methyl>-4,5-(isopropylidenedioxy)-2-cyclopentenyl>uracil 

Downstream Products

• 90597-22-1 cyclopentenyl cytosine 
• 115224-32-3 4-amino-1-<(1R,2R,3R)-2,3-dihydroxy-4-hydroxymethyl-4-cyclopenten-1-yl>-2(1H)-pyrimidinone 

Relevant articles and documents

Enhancing the Antiviral Efficacy of RNA-Dependent RNA Polymerase Inhibition by Combination with Modulators of Pyrimidine Metabolism

Many RNA virus infections lack suitable treatments. Liu et al. identified a host-targeting antiviral strategy of modulating pyrimidine metabolism with cyclopentenyl uracil, an inhibitor of pyrimidine salvage, and GSK983, an inhibitor of de novo biosynthesis. This combination also increased the potency of an RNA-dependent RNA polymerase inhibitor, against dengue virus.Genome-wide analysis of the mode of action of GSK983, a potent antiviral agent, led to the identification of dihydroorotate dehydrogenase as its target along with the discovery that genetic knockdown of pyrimidine salvage sensitized cells to GSK983. Because GSK983 is an ineffective antiviral in the presence of physiological uridine concentrations, we explored combining GSK983 with pyrimidine salvage inhibitors. We synthesized and evaluated analogs of cyclopentenyl uracil (CPU), an inhibitor of uridine salvage. We found that CPU was converted into its triphosphate in cells. When combined with GSK983, CPU resulted in large drops in cellular UTP and CTP pools. Consequently, CPU-GSK983 suppressed dengue virus replication in the presence of physiological concentrations of uridine. In addition, the CPU-GSK983 combination markedly enhanced the effect of RNA-dependent RNA polymerase (RdRp) inhibition on viral infection. Our findings highlight a new host-targeting strategy for potentiating the antiviral activity of RdRp inhibitors.

ENHANCING THE ANTIVIRAL EFFICACY OF RNA VIRUS INHIBITION BY COMBINATION WITH MODULATORS OF PYRIMIDINE METABOLISM

Compounds and methods are provided for the treatment of pathogenic virus infections. Compositions and methods are provided for inhibiting RNA viruses.

Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus

Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus are described. The key intermediate (-)- and (+)-cyclopentenyl alcohols (7 and 15) were prepared from D-γ-ribonolactone and D-ribose,

ENANTIOSELECTIVE SYNTHESIS OF NEW ANALOGS OF NEPLANOCIN A AND THEIR BIOLOGICAL ACTIVITY

Various carbocyclic nucleosides analogs of neplanocin A (such as 5-aminoimidazole-4-carboxamide riboside, uridine, 5-iodouridine, 4-thiouridine, cytidine, thymidine, 2'-deoxyguanosine, ribofuranosylthymine, a 2,2'-anhydroderivative, 2'-deoxycytidine, 2'-d