111379-66-9

Basic information

• Product Name: 5-amino-1-ribofuranosyl-1,2,4-triazole-3-carboxamidine
• Synonyms: 5-amino-1-ribofuranosyl-1,2,4-triazole-3-carboxamidine
• CAS NO: 111379-66-9
• Molecular Formula: C8H14 N6 O4 . Cl H
• Molecular Weight: 294.6955
• Mol File: 111379-66-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 667.6°Cat760mmHg
• Flash Point: 357.6°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 9.81E-19mmHg at 25°C
• CAS DataBase Reference: 5-amino-1-ribofuranosyl-1,2,4-triazole-3-carboxamidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-1-ribofuranosyl-1,2,4-triazole-3-carboxamidine(111379-66-9)
• EPA Substance Registry System: 5-amino-1-ribofuranosyl-1,2,4-triazole-3-carboxamidine(111379-66-9)

Safety Data

• Hazardous Substances Data: 111379-66-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H14N6O4.ClH/c9-5(10)6-12-8(11)14(13-6)7-4(17)3(16)2(1-15)18-7;/h2-4,7,15-17H,1H2,(H3,9,10)(H2,11,12,13);1H/t2-,3-,4-,7-;/m1./s1

Upstream product

• 52327-03-4 5-chloro-1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide 
• 111379-64-7 5-chloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide 
• 111379-65-8 5-chloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carbonitrile 

Relevant articles and documents

Synthesis and Evaluation of 5-Amino-1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamidine and Certain Related Nucleosides as Inhibitors of Purine Nucleoside Phosphorylase

The 5-amino and certain related derivatives of the powerful purine nucleoside phosphorylase (PNPase) inhibitor 1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamidine (TCNR, 3) have been prepared and evaluated for their PNPase activity.Acetylation followed by dehydration of 5-chloro-1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide (4a) gave 5-chloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carbonitrile (5).Ammonolysis of 5 furnished 5-amino-1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamidine (5-amino-TCNR, 6), the structure of which was assigned by single-crystal X-ray analysis.Acid-catalysed fusion of methyl 5-chloro-1,2,4-triazole-3-carboxylate (7a) with 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose (8) gave methyl 5-chloro-1-(2,3-di-O-acetyl-5-deoxy-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxylate (9a) and the corresponding positional isomer (9b).Transformation of the functional groups in 9a afforded a route to 5'-deoxyribavirin (9i).Compound 9a was converted in four steps to 5-amino-1-(5-deoxy-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamidine (5'-deoxy-5-amino-TCNR, 9g).Similar acid-catalysed fusion of 1,2,4-triazole-3-carbonitrile (7b) with 8 and ammonolysis of the reaction product 9h gave yet another route to 9i.Treatment of 9h with NH3/NH4Cl furnished 1-(5-deoxy-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamidine (5'-deoxy-TCNR, 9k).The C-nucleoside congener of TCNR (3-β-D-ribofuranosyl-1,2,4-triazole-5-carboxamidine, 12) was prepared in two steps from 3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-triazole-5-carbonitrile (10) by conventional procedure. 5-Amino-TCNR (6) displayed a more potent, high-affinity inhibition than TCNR, with a Ki of 10 μM.In contrast, 5'-deoxy-5-amino-TCNR (9g) was a significantly less potent inhibitor of PNPase, compared to 5'-deoxy-TCNR (Ki=80 and 20 μM, respectively).Neither the C-nucleoside congener of TCNR (12) nor that of ribavirin were found to inhibit inosine phosphorolysis.