3641-08-5

Usage

Uses

Used in Pharmaceutical Industry:
2H-1,2,4-Triazole-3-carboxamide is used as a building block or intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be incorporated into drug molecules, potentially enhancing their therapeutic properties and targeting specific biological pathways.
Used in Chemical Research:
In the field of chemical research, 2H-1,2,4-Triazole-3-carboxamide serves as a valuable compound for studying the properties and reactions of triazole-based molecules. Its reactivity and stability make it an interesting subject for exploration in organic chemistry.
Used in Antiviral Applications:
2H-1,2,4-Triazole-3-carboxamide is used as an antiviral agent, particularly in the synthesis of Ribavirin (R414475), a purine nucleoside analog. It inhibits inosine monophosphate dehydrogenase (IMPDH), which plays a crucial role in viral replication. 2H-1,2,4-Triazole-3-carboxamide is suitable for research related to pyruvate dehydrogenase (PDH) and its role in antiviral activity.
Used in Impurity Analysis:
N-Des-1-β-D-ribofuranosyl Ribavirin (Ribavirin EP Impurity D) is an impurity found in the synthesis of Ribavirin. As an impurity, 2H-1,2,4-Triazole-3-carboxamide may be used in the development and optimization of analytical methods for detecting and quantifying impurities in pharmaceutical products, ensuring their quality and safety.

InChI:InChI=1/C3H4N4O/c4-2(8)3-5-1-6-7-3/h1H,(H2,4,8)(H,5,6,7)

Upstream product

• 4928-88-5 methyl 1H-1,2,4-triazole-3-carboxylate 
• 36791-04-5 ribavirin 
• 515-96-8 oxalamic acid hydrazide 
• 16694-46-5 ethyl formimidate hydrochloride 

Downstream Products

• 578-76-7 7-methylguanine 
• 36791-04-5 ribavirin 
• 40372-11-0 1-(β-D-Arabinofuranosyl)-<1,2,4>triazol-3-carboxamid 
• 3641-10-9 1H-1,2,4-triazole-3-carbonitrile 
• 66-22-8 uracil 
• 4928-88-5 methyl 1H-1,2,4-triazole-3-carboxylate 
• 40372-06-3 1-(2'-deoxy-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide 
• 1006-08-2 7-methyl-1,7-dihydro-purin-6-one 

Relevant academic research and scientific papers

Synthesis of nucleotide analogues by a promiscuous phosphoribosyltransferase

An Escherichia coli strain overexpressing a mutant variant of a phosphoribosyl transferase was developed as a catalyst for the efficient preparation of a range of purine nucleotide analogues. This system offers an efficient and rapid method for nucleotide analogue synthesis with 100% β-selectivity, providing analytically pure product in a single purification step.

Dual-action mechanism of viramidine functioning as a prodrug and as a catabolic inhibitor for ribavirin

An investigational nucleoside analogue drug, viramidine, has recently emerged as a potentially safer alternative to ribavirin for the treatment of hepatitis C viral infection. We have reported that viramidine mainly functions as a prodrug of ribavirin that is enriched in the liver. This in vitro study further explores viramidine's activity against nucleoside pbosphorylase, a host enzyme that is responsible for phosphorolysis of ribavirin in vivo. Our experiments show that viramidine inhibits ribavirin phosphorolysis with a K i of 2.5 μM. This result suggests that viramidine may act through a dual-action mechanism by serving as a prodrug of ribavirin and concomitantly as an inhibitor for nucleoside phosphorylase catabolism of ribavirin.

Synthesis process of ribavirin intermediate and the intermediate

The invention discloses a synthesis process of a ribavirin intermediate and the intermediate. 2-hydrazinyl-2-oxoacetate is used as a raw material, and the ribavirin intermediate 1,2,4-triazole-3-formamide is obtained by condensation with orthoformate triester, ammonolysis and cyclization in sequence. According to the process, the 2-hydrazinyl-2-oxoacetate is adopted as the initial raw material, the raw material is easily available and cheap, the synthesis route is short, expensive raw materials such as hypophosphorous acid are not adopted, dangerous raw materials such as hydrogen peroxide arenot used, a diazotization reaction which is a dangerous process is not adopted, reaction condition is mild, the whole process is almost free of generation of wastewater and solid waste; and the process is green, simple to operate and high in yield.

Synthetic method of 1,2,4-triazole-3-formamide

The invention belongs to the preparation field of synthesis of key intermediates of an antiviral drug ribavirin and discloses a method for preparing 1,2,4-triazole-3-formamide. The method comprises the steps that under the effect of alkali, aminooxamide and ethyl formimidate hydrochloride produce cyclization reaction to generate the 1,2,4-triazole-3-formamide. According to the method, raw materials are easy to obtain, a synthesis route is short, posttreatment is convenient and simple, no pollution is produced during reaction, the amount of three wastes is small, and the preparation field is suitable for industrial production.

Method for preparing 1,2,4-triazole-3-formamide by one-pot method

The invention belongs to the field of the preparation of a key intermediate for synthesizing an antiviral drug ribavirin, and discloses a method for preparing 1,2,4-triazole-3-formamide by a one-pot method. The method comprises the following steps: performing a condensation reaction on oxamide and N,N-dimethylacetal, and under the action of a catalyst, enabling a product of the condensation reaction to perform a cyclization reaction with hydrazine or hydrazonium salt, and synthesizing the 1,2,4-triazole-3-formamide. The method is easy to obtain raw materials, short in synthetic route, convenient and simple in post-processing, non-polluted in reaction, less in three waste amount, and suitable for industrial production.

Chemoenzymatic method of 1,2,4-triazole nucleoside synthesis: Possibilities and limitations

Possibilities and limitations of chemoenzymatic synthesis of novel structural analogues of an antiviral preparation of Ribavirin (1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide) were established. A synthesis of various amides of 1H-1,2,4-triazole-3-carboxylic acid and its 5-substituted analogues - potential substrates of purine nucleoside phosphorylase - has been described. Comparative efficiency of preparation methods of these amides, as well as the methods of introduction of functional groups to the C5 position of heterocyclic system, were investigated. Novel analogues of Ribavirin containing various substitutes in the carboxamide group were synthesized. A biotechnological method was developed for the preparation of 1-β-D-ribofuranozyl-1,2,4-triazole-3-carbonitryl, an intermediate in the synthesis of Viramidine, the modern analogue of Ribavirin.

Enzymatic synthesis and antiviral activity of 2'-deoxy-2'-fluoro-ribavirin

2'-Deoxy-2'-fluoro-ribavirin has been efficiently synthesised from 2'-deoxy-2'-fluorouridine using nucleoside transferase as the key step, and evaluated for its antiviral properties in cell culture. An efficient synthesis of 3,5-di-O-p-chlorobenzoyl-2-deoxy-2-fluoro-β-D-ribofuranose is also described.

Process for preparing 1,2,4-triazole-3-carboxamides

There is disclosed a process for preparing a 1,2,4-triazole-3-carboxamide represented by the formula: STR1 wherein, R1 and R2 represent independently a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, or both R1 and R2 represent an alkylene group linked with each other directly or through an oxygen atom or a nitrogen atom to form a ring together with the nitrogen atom to which they are attached, which comprises subjecting an oxamohydrazide represented by the formula: STR2 wherein R1 and R2 have the same meanings as defined above, to reaction with formamidine or a salt thereof.