59211-02-8

Basic information

• Product Name: 1-[2,3,5-tris-O-(methylsulfonyl)pentofuranosyl]pyrimidine-2,4(1H,3H)-dione
• CAS NO: 59211-02-8
• Molecular Formula: C₁₂H₁₈N₂O₁₂S₃
• Molecular Weight: 478.4725
• Mol File: 59211-02-8.mol
• Article Data: 1

Chemical Properties

• Density: 1.73g/cm³
• Refractive Index: 1.601
• CAS DataBase Reference: 1-[2,3,5-tris-O-(methylsulfonyl)pentofuranosyl]pyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2,3,5-tris-O-(methylsulfonyl)pentofuranosyl]pyrimidine-2,4(1H,3H)-dione(59211-02-8)
• EPA Substance Registry System: 1-[2,3,5-tris-O-(methylsulfonyl)pentofuranosyl]pyrimidine-2,4(1H,3H)-dione(59211-02-8)

Safety Data

• Hazardous Substances Data: 59211-02-8(Hazardous Substances Data)

Usage

Chemical structure

A pyrimidine-2,4(1H,3H)-dione molecule attached to a complex sugar structure.

Sugar component

Composed of pentofuranosyl units.

Modification

Each pentofuranosyl unit is modified with three methylsulfonyl groups.

Classification

A nucleoside analog.

Synthesis

Synthesized for potential use in pharmaceutical research.

Potential applications

Exhibits antiviral and anticancer properties, making it of interest for drug development.

Scientific value

The intricate structure makes it a challenging and valuable compound for scientific study.

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 58-96-8 uridine 

Downstream Products

• 84045-20-5 1-(5-benzamido-5-deoxy-2,3-epoxy-β-D-lyxofuranosyl)uracil 
• 141917-21-7 1-(5-azido-3-benzamido-3,5-dideoxy-β-D-arabinofuranosyl)uracil 
• 141917-25-1 1-(3-azido-5-benzamido-3,5-dideoxy-β-D-arabinofuranosyl)uracil 
• 141917-27-3 1-(2-O-acetyl-3-amino-5-benzamido-3,5-dideoxy-β-D-arabinofuranosyl)uracil 
• 141917-22-8 1-(5-azido-2-benzamido-2,5-dideoxy-β-D-xylofuranosyl)uracil 
• 84045-15-8 2,2'-anhydro-1-(5-benzamido-5-deoxy-3-O-methanesulfonyl-β-D-arabinofuranosyl)uracil 
• 141917-36-4 2,5'-imino-1-(2-O-benzoyl-3-O-methylsulfonyl-β-D-arabinofuranosyl)uracil 
• 141917-18-2 1-(5-benzamido-5-deoxy-3-methylsulfonyl-β-D-arabinofuranosyl)uracil 
• 141917-26-2 1-(2-O-acetyl-3-azido-5-benzamido-3,5-dideoxy-β-D-arabinofuranosyl)uracil 
• 141917-40-0 1-(5-deoxy-5-diphenylphosphoramido-2,3-epoxy-β-D-lyxofuranosyl)uracil 
• 141917-28-4 1-(2-O-acetyl-3,5-dibenzamido-3,5-dideoxy-β-D-arabinofuranosyl)uracil 
• 141917-38-6 5'-N-benzoyl-2,5'-imino-1-(2-O-benzoyl-3-O-methylsulfonyl-β-D-arabinofuranosyl)uracil 
• 141917-39-7 2,2'-anhydro-1-(5-deoxy-5-diphenylphosphoramido-3-O-methylsulfonyl-β-D-arabinofuranosyl)uracil 
• 141917-41-1 1-(2-O-acetyl-5-benzamido-3,5-dideoxy-3-diphenylphosphoramido-β-D-arabinofuranosyl)uracil 

Relevant articles and documents

[d4U]-Spacer-[HI-236] double-drug inhibitors of HIV-1 reverse-transcriptase

Four double-drug HIV NRTI/NNRTI inhibitors 15a-d of the type [d4U]-spacer-[HI-236] in which the spacer is varied as 1-butynyl (15a), propargyl-1-PEG (15b), propargyl-2-PEG (15c) and propargyl-4-PEG (15d) have been synthesized and biologically evaluated as RT inhibitors against HIV-1. The key step in their synthesis involved a Sonogashira coupling of 5-iodo d4U's benzoate with an alkynylated tethered HI-236 precursor followed by introduction of the HI-236 thiourea functionality. Biological evaluation in both cell-culture (MT-2 cells) as well as using an in vitro RT assay revealed 15a-c to be all more active than d4T. However, overall the results indicate the derivatives are acting as chain-extended NNRTIs in which for 15b-d the nucleoside component is likely situated outside of the pocket but with no evidence for any synergistic double binding between the NRTI and NNRTI sites. This is attributed, in part, to the lack of phosphorylation of the nucleoside component of the double-drug as a result of kinase recognition failure, which is not improved upon with the phosphoramidate of 15d incorporating a 4-PEG spacer.