13924-96-4

Basic information

• Product Name: Pyrazinecarboxamide, 4,5-dihydro-5-oxo
• Synonyms: 5-Hydroxypyrazinamide;Pyrazinecarboxamide, 4,5-dihydro-5-oxo
• CAS NO: 13924-96-4
• Molecular Formula: C₅H₅N₃O₂
• Molecular Weight: 139.1121
• Mol File: 13924-96-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 292-295 °C
• Boiling Point: 659 °C at 760 mmHg
• Flash Point: 352.4 °C
• Appearance: /
• Density: 1.63 g/cm³
• Vapor Pressure: 5.65E-18mmHg at 25°C
• Refractive Index: 1.696
• PKA: 10.69±0.40(Predicted)
• CAS DataBase Reference: Pyrazinecarboxamide, 4,5-dihydro-5-oxo(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrazinecarboxamide, 4,5-dihydro-5-oxo(13924-96-4)
• EPA Substance Registry System: Pyrazinecarboxamide, 4,5-dihydro-5-oxo(13924-96-4)

Safety Data

• Hazardous Substances Data: 13924-96-4(Hazardous Substances Data)

Usage

Uses

5-Hydroxypyrazinecarboxamide is a metabolite of Pyrazinamide (P840600), an antibacterial (tuberculostatic).

InChI:InChI=1/C5H5N3O2/c6-5(10)3-1-8-4(9)2-7-3/h1-2H,(H2,6,10)(H,8,9)

Upstream product

• 57005-60-4 1,6-dihydro-6-oxo-2,3-pyrazinedicarbonitrile 
• 77168-76-4 3-carbamoyl-1,6-dihydro-6-oxo-2-pyrazinecarboxylic acid 

Downstream Products

• 13924-95-3 methyl 4,5-dihydro-5-oxo-2-pyrazinecarboxylate 
• 77168-80-0 5,6-dihydroxy-2-pyrazinecarboxylic acid 
• 33332-25-1 methyl 5-chloropyrazine-2-carboxylate 
• 34604-60-9 4,5-dihydro-5-oxo-2-pyrazinecarboxylic acid 

Relevant articles and documents

Discovery of pyrimidine nucleoside dual prodrugs and pyrazine nucleosides as novel anti-HCV agents

To explore the application potential of dual prodrug strategies in the development of anti-HCV agents, a variety of sofosbuvir derivatives with modifications at the C4 or N3 position of the uracil moiety were designed and synthesized. Some compounds exhibited potent anti-HCV activities, such as 4e and 8a–8c with similar EC50 values (0.20–0.22 μM) comparative to that of sofosbuvir (EC50 = 0.18 μM) in a genotype 1b based replicon Huh-7 cell line. Moreover, 8b displayed a good human plasma stability profile, and was easily metabolized in human liver microsomes expectantly. On the other hand, aiming to discover novel anti-HCV nucleosides, pyrazin-2(1H)-one nucleosides and their phosphoramidate prodrugs were investigated. Several active compounds were discovered, such as 25e (EC50 = 7.3 μM) and S-29b (EC50 = 19.5 μM). This kind of nucleosides were interesting and would open a new avenue for the development of antiviral agents.