120362-25-6

Basic information

• Product Name: methyl 1-ribofuranosyl-1,2,4-triazole-3-carboxamidate
• Synonyms: methyl 1-ribofuranosyl-1,2,4-triazole-3-carboxamidate
• CAS NO: 120362-25-6
• Molecular Formula: C9H14 N4 O5
• Molecular Weight: 258.23
• Mol File: 120362-25-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 150-153 °C
• Boiling Point: 526.7°C at 760 mmHg
• Flash Point: 272.3°C
• Appearance: /
• Density: 1.82g/cm³
• Vapor Pressure: 6.37E-12mmHg at 25°C
• Refractive Index: 1.722
• PKA: 12.94±0.70(Predicted)
• CAS DataBase Reference: methyl 1-ribofuranosyl-1,2,4-triazole-3-carboxamidate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 1-ribofuranosyl-1,2,4-triazole-3-carboxamidate(120362-25-6)
• EPA Substance Registry System: methyl 1-ribofuranosyl-1,2,4-triazole-3-carboxamidate(120362-25-6)

Safety Data

• Hazardous Substances Data: 120362-25-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H14N4O5/c1-17-7(10)8-11-3-13(12-8)9-6(16)5(15)4(2-14)18-9/h3-6,9-10,14-16H,2H2,1H3/b10-7-/t4-,5-,6-,9-/m1/s1

Upstream product

• 40371-99-1 3-cyano-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-triazole 
• 36791-04-5 ribavirin 
• 40372-03-0 2',3',5'-Tri-O-acetyl-1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide 
• 124-41-4 sodium methylate 

Downstream Products

• 40372-00-7 ribamidine hydrochloride 
• 36791-04-5 ribavirin 

Relevant articles and documents

Synthesis and Antiviral Evaluation of N-Carboxamidine-Substituted Analogues of 1-β-D-Ribofuranosyl-1,2,4-triazole-3-carboxamidine Hydrochloride

Ten, hitherto unreported, analogues of 1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamidine hydrochloride (2a, ribamidine) and methyl carboxamidate 5 have been synthesized.These include the N-cyano (2b), N-alkyl (2c-e), N-amino acid (2f-h), N,N'-disubstituted (6,7a,b), and the N-methylated carboxamide (1f) analogues of ribavirin.In addition, a new facile synthesis of carboxamidine 2a was also developed.All compounds were evaluated for biological activity against the following RNA viruses: Punta Toro (PT) and sandfly fever (SF) viruses (bunyaviruses); Japanese encephalitis (JE), yellow fever (YF), and dengue-4 viruses (flaviviruses); parainfluenza type 3 (PIV3), respiratory syncytial virus (RSV), and measles viruses (paramyxoviruses); influenza A and B viruses (orthomyxoviruses); Venezuelan equine encephalomyelitis virus (VEE, alphavirus); human immunodeficiency virus type-1 (HIV-1, lentivirus); the DNA-containing vaccina (VV) virus (poxvirus); and adeno type-5 (Ad5) viruses.All of the compounds except for 2a and 7a,b exhibited activity against the bunyaviruses such as that observed with 2a; however, higher IC50 values were generally observed.Glycine analogue 2f showed activity in PT-virus-infected mice in therms of increased survivors and descreased markers of viral pathogenicity.Carboxamidine 2a, carboximidate 5, and dimethyl amidine 6 exhibited activity against dengue type-4 virus.Monomethyl amidine 2c demonstrated activity against RSV, PIV3, and, to a lesser extent, influenza A and B.Activity of 2c generally required higher IC50 values than unsubstituted 2a.The latter exhibited hitherto unreported activity against RSV; therapeutic indices for 2a against RSV and PIV3 were >64 and >21.No substantial in vitro activity was observed for any of the compounds tested against Ad5, measles, JE, YF, VEE, or HIV-1.In addition, evidence is presented which argues in favor of a distinct antiviral mechanism of action for carboxamidines, e.g. 6, in contrast to a role as a carboxamide precursor.

Oligomer conjugates of heteropentacyclic nucleosides

The invention provides small molecule drugs that are chemically modified by covalent attachment of a water-soluble oligomer.