15147-68-9

Basic information

• Product Name: 2-[5-O-(methylsulfonyl)pentofuranosyl]-1,2,4-triazine-3,5(2H,4H)-dione
• CAS NO: 15147-68-9
• Molecular Formula: C₉H₁₃N₃O₈S
• Molecular Weight: 323.2798
• Mol File: 15147-68-9.mol
• Article Data: 1

Chemical Properties

• Density: 1.99g/cm³
• Refractive Index: 1.729
• CAS DataBase Reference: 2-[5-O-(methylsulfonyl)pentofuranosyl]-1,2,4-triazine-3,5(2H,4H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[5-O-(methylsulfonyl)pentofuranosyl]-1,2,4-triazine-3,5(2H,4H)-dione(15147-68-9)
• EPA Substance Registry System: 2-[5-O-(methylsulfonyl)pentofuranosyl]-1,2,4-triazine-3,5(2H,4H)-dione(15147-68-9)

Safety Data

• Hazardous Substances Data: 15147-68-9(Hazardous Substances Data)

Usage

General Description

2-[5-O-(methylsulfonyl)pentofuranosyl]-1,2,4-triazine-3,5(2H,4H)-dione is a chemical compound with the molecular formula C8H10N4O6S. It is a potent inhibitor of inosine monophosphate dehydrogenase, an enzyme involved in the de novo synthesis of guanine nucleotides. This makes it an important drug for the treatment of autoimmune diseases like rheumatoid arthritis and inflammatory bowel disease, as well as for the prevention of organ transplant rejection. The compound is also being researched for its potential anti-cancer properties, as it has shown to be effective in inhibiting the proliferation of cancer cells in pre-clinical studies.

Upstream product

• 59967-97-4 6-azauridine 2',3'-O-carbonate 
• 59967-98-5 5'-O-methanesulfonyl-2',3'-O-carbonyl-6-azauridine 

Relevant articles and documents

2',3'-O-CARBONYL DERIVATIVES OF 6-AZAURIDINE IN THE SYNTHESIS OF ITS 5'-SUBSTITUTED AND 5'-DEOXY DERIVATIVES

Preparation of 2',3'-O-carbonyl derivatives of 5'-deoxy-6-azauridine and 6-azauridine using 1,1'-carbonyldiimidazole has been elaborated. 5'-Chloro and 5'-bromo derivatives were prepared by treatment of the 5'-O-mesyl derivative with quarternary ammonium halides, 5'-chloro derivatives also by direct halogenation with thionyl chloride in hexamethylphosphortriamide or with tetrachloromethane, triphenyl phosphine, and dimethylformamide.Derivatives of 5'-bromo-6-azauridine were reduced with tributyltin hydride to 5'-deoxy-6-azauridine compounds. 6-Azauridine 2',3'-carbonate (IVa) and its 5'-derivatives IVc and IVe on treatment with imidazole in dimethylformamide afforded 2,2'-anhydronucleosides IIIa-IIIc.The 2,2'-anhydro-5'-deoxy compound IIIc underwent alkaline hydrolysis to 5'-deoxy-1-β-D-arabino-pentofuranosyl-6-azauracil (VIa).Treatment of 2,2'-anhydro-5'-deoxy-5'-chloro derivative IIIb with hydrogen chloride led to 2',5'-dichloro derivative If.