4342-07-8

Basic information

• Product Name: 5-AMINO-1-METHYL-1H-1,2,3-TRIAZOLE-4-CARBOXAMIDE
• Synonyms: 5-AMINO-1-METHYL-1H-1,2,3-TRIAZOLE-4-CARBOXAMIDE;TOSLAB 27061;5-amino-2H-triazole-4-carboxamide;5-Amino-1H-triazole-4-carboxamide
• CAS NO: 4342-07-8
• Molecular Formula: C₃H₅N₅O
• Molecular Weight: 141.13
• Mol File: 4342-07-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 478.2°Cat760mmHg
• Flash Point: 243°C
• Appearance: /
• Density: 1.69g/cm³
• Vapor Pressure: 2.62E-09mmHg at 25°C
• Refractive Index: 1.73
• CAS DataBase Reference: 5-AMINO-1-METHYL-1H-1,2,3-TRIAZOLE-4-CARBOXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-1-METHYL-1H-1,2,3-TRIAZOLE-4-CARBOXAMIDE(4342-07-8)
• EPA Substance Registry System: 5-AMINO-1-METHYL-1H-1,2,3-TRIAZOLE-4-CARBOXAMIDE(4342-07-8)

Safety Data

• Hazardous Substances Data: 4342-07-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C3H5N5O/c4-2-1(3(5)9)6-8-7-2/h(H2,5,9)(H3,4,6,7,8)

Upstream product

• 2683-90-1 8-azahypoxanthine 
• 134-58-7 8-azaguanine 
• 4342-08-9 4-amino-3-benzyl-1,2,3-triazole-5-carboxamide 
• 1468-26-4 8-azaxanthine 

Downstream Products

• 135340-74-8 5-Amino-1-[3-chloro-4-(2,4-dichloro-benzoyl)-benzyl]-1H-[1,2,3]triazole-4-carboxylic acid amide 
• 135340-76-0 5-Amino-1-[4-(2,4,6-trichloro-benzoyl)-benzyl]-1H-[1,2,3]triazole-4-carboxylic acid amide 
• 135340-66-8 5-Amino-1-[3-chloro-4-(4-chloro-benzoyl)-5-fluoro-benzyl]-1H-[1,2,3]triazole-4-carboxylic acid amide 
• 2683-90-1 8-azahypoxanthine 
• 424830-85-3 4⁽⁵⁾-Benzoylamino-5⁽⁴⁾-carboxyamido-1H-1,2,3-triazole 
• 1426343-27-2 9-phenyl-4,5,6,7,8,9-hexahydro[1,2,3]triazolo[5,1-b]quinazoline-3-carboxamide 
• 1426343-37-4 9-(4-chlorophenyl)-6,6-dimethyl-8-oxo-4,5,6,7,8,9-hexahydro[1,2,3]triazolo[5,1-b]quinazoline-3-carboxamide 
• 1426343-32-9 9-(4-chlorophenyl)-8-oxo-4,5,6,7,8,9-hexahydro[1,2,3]triazolo[5,1-b]quinazoline-3-carboxamide 
• 1426343-36-3 9-(4-bromophenyl)-6,6-dimethyl-8-oxo-4,5,6,7,8,9-hexahydro[1,2,3]triazolo[5,1-b]quinazoline-3-carboxamide 
• 1426343-31-8 9-(4-bromophenyl)-8-oxo-4,5,6,7,8,9-hexahydro[1,2,3]triazolo[5,1-b]quinazoline-3-carboxamide 
• 1426343-35-2 9-(2-methoxyphenyl)-6,6-dimethyl-8-oxo-4,5,6,7,8,9-hexahydro[1,2,3]triazolo[5,1-b]quinazoline-3-carboxamide 
• 1426343-30-7 9-(2-methoxyphenyl)-8-oxo-4,5,6,7,8,9-hexahydro[1,2,3]triazolo[5,1-b]quinazoline-3-carboxamide 
• 1426343-34-1 9-(4-methoxyphenyl)-6,6-dimethyl-8-oxo-4,5,6,7,8,9-hexahydro[1,2,3]triazolo[5,1-b]quinazoline-3-carboxamide 
• 1426343-29-4 9-(4-methoxyphenyl)-8-oxo-4,5,6,7,8,9-hexahydro[1,2,3]triazolo[5,1-b]quinazoline-3-carboxamide 

Relevant articles and documents

Benzylated 1,2,3-triazoles as anticoccidiostats

Substituted 5-amino-4-carbamoyl-1,2,3-triazoles 3a-w were prepared by two synthetic schemes and evaluated in vivo for anticoccidial activity. Both schemes proceeded by brominating appropriately substituted toluenes 4a-s,v to 5a-s,v. In Scheme I, the brominated benzyl analogues 5 were converted to the corresponding benzyl azides 6, which were treated with cyanoacetamide to yield 1-substituted-5-amino-4-carbamoyl-1,2,3-triazoles 3. In Scheme II, the benzyl halides 5 were employed to alkylate the sodium salt of 5-amino-4-carbamoyl-1,2,3-triazole (7). Preliminary screening data against Eimeria acervulina and E. tenella in chickens suggested structural requirements for maximizing activity. Further evaluation against a relatively resistant series of eight Eimeria field isolates revealed L-651,582 (3a) to be a highly effective coccidiostat. However, unacceptable tissue residues precluded further development. Mechanistic studies on this series of 5-amino-4-carbamoyl-1,2,3-triazoles and, in particular, on L-651,582 (3a) revealed that its mode of action does not involve inhibition of IMP dehydrogenase, but probably interferes with host cell calcium entry. In addition, L-651,582 has been found to have antiproliferative activity in several disease models and was recently reported to possess antimetastatic activity in a model of ovarian cancer progression.