49607-51-4

Usage

Uses

Used in Pharmaceutical Industry:
1-Methyl-1H-1,2,4-triazol-3-amine is used as a building block for the synthesis of various pharmaceuticals due to its unique chemical structure and reactivity. Its presence in the molecular composition of drugs can contribute to their therapeutic effects, including antifungal and anticancer properties.
Used in Agrochemical Industry:
In the agrochemical sector, 1-Methyl-1H-1,2,4-triazol-3-amine is utilized as a key component in the development of compounds that protect crops from fungal infections. Its antifungal properties make it a valuable asset in the creation of effective agricultural products.
Used in Organic Synthesis:
1-Methyl-1H-1,2,4-triazol-3-amine is employed as a versatile intermediate in organic synthesis for the preparation of a wide range of organic compounds. Its chemical properties allow it to participate in various reactions, facilitating the creation of complex molecules for different applications.
Used in Research Applications:
1-Methyl-1H-1,2,4-triazol-3-amine is also used in research settings for studying its biological activities and exploring its potential in the development of new therapeutic agents. The ongoing research on 1-Methyl-1H-1,2,4-triazol-3-amine aids in understanding its mechanisms of action and its interactions with biological systems, which can lead to the discovery of novel applications in medicine and other fields.

Upstream product

• 26621-45-4 methyl-3-nitro-1H-1,2,4-triazole 

Downstream Products

• 1295541-98-8 C₁₅H₁₂ClF₃N₆O 

Relevant academic research and scientific papers

Structure-activity relationships of triazole-benzodioxine inhibitors of cathepsin X

Cathepsin X is a cysteine carboxypeptidase that is involved in various physiological and pathological processes. In particular, highly elevated expression and activity of cathepsin X has been observed in cancers and neurodegenerative diseases. Previously, we identified compound Z9 (1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-((4-isopropyl-4H-1,2,4-triazol-3-yl)thio)ethan-1-one) as a potent and specific reversible cathepsin X inhibitor. Here, we have explored the effects of chemical variations to Z9 of either benzodioxine or triazol moieties, and the importance of the central ketomethylenethio linker. The ketomethylenethio linker was crucial for cathepsin X inhibition, whereas changes of the triazole heterocycle did not alter the inhibitory potencies to a greater extent. Replacement of benzodioxine moiety with substituted benzenes reduced cathepsin X inhibition. Overall, several synthesized compounds showed similar or improved inhibitory potencies against cathepsin X compared to Z9, with IC50 values of 7.1 μM–13.6 μM. Additionally, 25 inhibited prostate cancer cell migration by 21%, which is under the control of cathepsin X.

Tuning azoheteroarene photoswitch performance through heteroaryl design

Photoswitchable compounds, which can be reversibly switched between two isomers by light, continue to attract significant attention for a wide array of applications. Azoheteroarenes represent a relatively new but understudied type of photoswitch, where one of the aryl rings from the conventional azobenzene class has been replaced with a fivemembered heteroaromatic ring. Initial studies have suggested the azoheteroarenes-the arylazopyrazoles in particular- to have excellent photoswitching properties (quantitative switching and long Z isomer half-life). Here we present a systematic computational and experimental study to elucidate the origin of the long thermal half-lives and excellent addressability of the arylazopyrazoles, and apply this understanding to determine important structure-property relationships for a wide array of comparable azoheteroaryl photoswitches. We identify compounds with Z isomer half-lives ranging from seconds to hours, to days and to years, and variable absorption characteristics, all through tuning of the heteraromatic ring. Conformation perhaps plays the largest role in determining such properties: the compounds with the longest isomerization half-lives adopt a T-shaped ground state Z isomer conformation and proceed through a T-shaped isomerization pathway, whereas the most complete photoswitching is achieved for compounds that have a twisted (rather than T-shaped) Z isomer conformation. By balancing these factors, we report a new azopyrazole 3pzH, which can be quantitatively switched to its Z isomer (1/2 = 74 d at 25 °C). Given the large tunability of their properties, the predictive nature of their performance, and the other functional opportunities afforded by usage of a heteroaromatic system, we believe the azoheteroaryl photoswitches to have huge potential in a wide range of optically addressable applications.

Deacetylcolchicine deriv.

Provided are 4-modified colchicine compounds and medicines using the same. Specifically provided are colchicine derivatives represented by general formula (1), salts thereof, and solvates of the same. In general formula (1), R1 is a halogen atom, a hydroxyl group, a nitro group, an amino group, or a mono-, di- or tri-fluoromethyl group; R2, R3 and R4 are each a methoxy group or a hydroxyl group, or alternatively R2 and R3, or R3 and R4 together represent a methylenedioxy group; R5 and R6 may be the same or different and are each a hydrogen atom, a C1-6 alkyl group, an arylalkyl group, a C2-6 alkenyl group, -COR7, -COOR8, -SO2R9, -CONR10R11, or -CSNR12R13, or alternatively R5 and R6 together with the nitrogen atom to which R5 and R6 are bonded may form a three- to seven-membered cyclic amino group; R7 is a C1-6 alkyl group or the like; R8 is a C1-6 alkyl group or the like; R9 is a C1-6 alkyl group or the like; R10 and R11 may be the same or different and are each a hydrogen atom, a C1-6 alkyl group, or the like; and R12 and R13 may be the same or different and are each a hydrogen atom, an alkyl group, or the like.

Design and synthesis of highly potent and isoform selective JNK3 inhibitors: SAR studies on aminopyrazole derivatives

The c-jun N-terminal kinase 3 (JNK3) is expressed primarily in the brain. Numerous reports have shown that inhibition of JNK3 is a promising strategy for treatment of neurodegeneration. The optimization of aminopyrazole-based JNK3 inhibitors with improved potency, isoform selectivity, and pharmacological properties by structure-activity relationship (SAR) studies utilizing biochemical and cell-based assays, and structure-based drug design is reported. These inhibitors had high selectivity over JNK1 and p38α, minimal cytotoxicity, potent inhibition of 6-OHDA-induced mitochondrial membrane potential dissipation and ROS generation, and good drug metabolism and pharmacokinetic (DMPK) properties for iv dosing. 26n was profiled against 464 kinases and was found to be highly selective hitting only seven kinases with >80% inhibition at 10 μM. Moreover, 26n showed good solubility, good brain penetration, and good DMPK properties. Finally, the crystal structure of 26k in complex with JNK3 was solved at 1.8 ? to explore the binding mode of aminopyrazole based JNK3 inhibitors.

Thiazole-4-carboxyamide derivatives

The present invention is concerned with novel thiazole 4-carboxyamide derivatives of the general formula (I) and with methods for the preparation thereof, which compounds are useful as metabotropic glutamate receptor antagonists: wherein R1 to R4 are as defined in the specification.

Imidazole, triazole and tetrazole derivatives

A class of substituted imidazole, triazole and tetrazole derivatives are selective agonists of 5-HT1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a

DIAZO COMPOUNDS IN THE 1,2,4-TRIAZOLE SERIES. II. STRUCTURE AND TRANSFORMATIONS OF THE PRODUCTS FROM DIAZOTIZATION OF 1-METHYL-3-AMINO-5-R-1,2,4-TRIAZOLES

Unstable solutions of diazonium salts are formed during the diazotization of 1-methyl-3-amino-5-R-1,2,4-triazoles.When treated with alkali, the diazonium salts change into the Z- and E-diazoates.The pKa values for the E-diazoate-E-diazohydroxide equilibrium were determined.Acidification of solutions of the E-diazohydroxides leads the diazonium salts.In the pH region where the joint presence of the diazohydroxide and diazonium forms is possible the solutions of the diazo compounds exhibited enhanced instability.