3641-14-3

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 5-amino-1H-1,2,4-triazole-3-carboxylate is utilized as a building block for the synthesis of various pharmaceuticals. Its role in the development of new drugs is significant due to its ability to contribute to the formation of complex molecular structures that can address a range of medical needs.
Used in Agrochemical Industry:
In the agrochemical sector, Methyl 5-amino-1H-1,2,4-triazole-3-carboxylate serves as an intermediate in the production of herbicides and plant growth regulators. Its incorporation into these products helps in the management of weed populations and the enhancement of crop yields, contributing to more efficient agricultural practices.
Used in Organic Synthesis:
Methyl 5-amino-1H-1,2,4-triazole-3-carboxylate is also employed in organic synthesis for its versatile reactivity. This allows chemists to create a variety of compounds with different applications across multiple industries, showcasing the compound's adaptability and importance in chemical research and development.

InChI:InChI=1/C4H6N4O2/c1-10-3(9)2-6-4(5)8-7-2/h1H3,(H3,5,6,7,8)

Upstream product

• 67-56-1 methanol 
• 3641-13-2 3-amino-1,2,4-triazole-5-carboxylic acid 
• 3641-13-2 5-amino-1H-[1,2,4]triazole-3-carboxylic acid 

Downstream Products

• 304696-18-2 5-(3-benzyl-ureido)-2H-[1,2,4]triazole-3-carboxylic acid methyl ester 
• 473994-45-5 methyl [1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate 
• 1020171-17-8 C₃₂H₃₂N₄O₆ 
• 1020171-19-0 C₃₂H₃₂N₄O₆ 
• 60016-63-9 3-Amino-5-carbamoyl-1,2,4-triazol 
• 704911-47-7 methyl 3-bromo-1H-1,2,4-triazole-5-carboxylate 
• 1354692-80-0 5-{[(2R,3S,4R,5S)-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-1-methyl-pyrrolidine-2-carbonyl]-amino}-2H-[1,2,4]triazole-3-carboxylic acid methyl ester 
• 3641-15-4 3-amino-1H-1,2,4-triazole-5-carbohydrazide 
• 53566-46-4 methyl 5-azido-1H-1,2,4-triazole-3-carboxylate 
• 704911-47-7 methyl 5-bromo-1H-1,2,4-triazole-3-carboxylate 
• 921225-11-8 (5-amino-1H-1,2,4-triazol-3-yl)(morpholino)methanone 
• 114040-29-8 ethyl 5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate 
• 1337957-20-6 6,6-dimethyl-8-oxo-9-p-tolyl-(4,5,6,7,8,9-hexahydro-[1,2,4]triazolo[5,1-b]quinazoline)-2-carboxylic acid methyl ester 
• 1311315-62-4 methyl-4Н-[1,2,4]triazolo[5,1-с][1,2,4]benzothiadiazine-2-carboxylate 5,5-dioxide 

Relevant academic research and scientific papers

Design, synthesis and mechanistic study of new 1,2,4-triazole derivatives as antimicrobial agents

Novel 5-amino-1,2,4-triazole derivatives and their cyclized 1,2,4-triazolo[1,5-a]pyrimidine analogues were designed, synthesized and evaluated for their antimicrobial activities. They were tested against five bacterial strains (Methicillin Resistant S. aureus (MRSA), E. coli, K. pneumoniae, A. baumannii and P. aeruginosa) using ciprofloxacin as a positive control and against two fungal strains (C. albicans and C. neoformans) using fluconazole and amphotericin B as positive controls. Compounds 9, 13a and 13b showed high to moderate antifungal activities against candida albicans (MIC values = 4–32 μg/ml), with considerable safety profiles; where no cytotoxicity against human embryonic kidney or red blood cells were detected at concentrations up to 32 μg/mL. Furthermore, compound 9 showed significant inhibitory activity against lansterol 14α-demethylase (IC50 = 0.27 μM), compared to the reference drug fluconazole (IC50 = 0.25 μM). Molecular docking of compound 9 into the active site of the cytochrome P450 enzyme revealed comparable binding modes and docking scores to those of fluconazole. Finally, in silico ADME studies prediction and drug-like properties of these compounds revealed favorable oral bioavailability results.

Synthesis, structure and properties of N-acetylated derivatives of methyl 5-amino-1H-[1,2,4]triazole-3-carboxylate

Methyl 5-amino-1H-[1,2,4]triazole-3-carboxylate hydrochloride (1) and free ester (2) were obtained and 2 was reacted with Ac2O to give the acetylated products 3-6. Compounds 1-6 were studied using HPLC, GCMS, FTIR and multinuclear NMR spectroscopy, including the cross-polarisation magic angle spinning (CPMAS) technique. The results of the acetylation of 2 were compared to those of the acetylation of 5-amino-1H-[1,2,4]triazole, and for 2 a significant decrease in the susceptibility to acetylation was found. The reaction of 2 with Ac2O at 20°C, regardless of the amount and the concentration of the latter, including neat Ac2O, proceeds fully regioselectively and leads to one product: methyl 1-acetyl-5-amino-1H-[1,2,4]triazole-3-carboxylate (3). In sharp contrast to 5-amino-1H-[1,2,4]triazole, neither an additional monoacetylated isomer, whether annular or exocyclic, nor any diacetylated derivative could be detected. The diacetylation of 2 requires the process to be carried out in neat boiling Ac2O and, as in the case of 5-amino-1H-[1,2,4]triazole, gives two diacetylated isomers. These are methyl 1-acetyl-3-(acetylamino)-1H-[1,2,4]triazole-5-carboxylate (4) and 1-acetyl-5-(acetylamino)-1H-[1,2,4]triazole-3-carboxylate (5). Hypothetical pathways of their formation have been suggested. A mixture of 4 and 5 upon hydrolysis of the ring acetyl group gives the monoacetylated derivative methyl 5-(acetylamino)-1H-[1,2,4]triazole-3-carboxylate (6). The spectroscopic, structural and conformational characteristics of compounds 1-6 have been given and methods for their preparation have been provided.

Synthesis of esters and amides of 5-amino-1,2,4-triazole-3-carboxylic and 5-amino-1,2,4-triazol-3-ylacetic acids

Various synthetic routes to esters and amides of 5-amino-1,2,4-triazole-3- carboxylic and 5-amino-1,2,4-triazol-3-ylacetic acids were examined. Pleiades Publishing, Inc., 2006.

Nitrogen-rich energetic material 3-amino-3'-nitroamino-5,5'-bi-1,2,4-triazole and preparation method thereof

The invention discloses a nitrogen-rich energetic material 3-amino-3'-nitroamino-5,5'-bi-1,2,4-triazole and a preparation method thereof. The energetic material is synthesized for the first time. Tests show that 3-amino-3'-nitroamino-5,5'-bi-1,2,4-triazole is an insensitive energetic material having good thermal stability and meeting the requirement of insensitive energetic materials. The materialhas impact sensitivity of 80J and friction sensitivity of 360N. In view of the good characteristics of the compound, the preparation method of the material is very important. A reliable and cheap synthetic route suitable for amplification is developed for the compound, the target product is obtained from commercially available raw material 5-amino-1,2,4-triazolyl-3-formic acid as a start by esterification catalyzed by concentrated sulfuric acid, hydrazinolysis of hydrazine hydrate and ring-closing reaction of N-methyl-N-nitro-N-nitrosoguanidine, the raw materials are simple and easy to obtain, the price is low, and the total reaction yield can be as high as 49%.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

Synthesis of highly potent and selective hetaryl ureas as integrin αVβ3-receptor antagonists

Solid-phase synthesis and SAR of integrin αVβ3-receptor antagonists containing a urea moiety as non-basic guanidine mimetic are described. The most potent compounds exhibited IC50 values towards αVβ3 in the nanomolar range and high selectivity versus related integrins like αIIbβ3. For selected examples efficacy in functional cellular assays is demonstrated.