35607-27-3

Usage

Uses

Used in Pharmaceutical Industry:
5-(Pyridin-3-yl)-4H-1,2,4-triazol-3-amine is used as a key intermediate in the synthesis of various pharmaceutical drugs for its antimicrobial, anticancer, and anti-inflammatory properties. Its unique structural features and versatile properties make it a promising candidate for the development of new therapeutic compounds to treat a variety of diseases.
Used in Agrochemical Industry:
5-(Pyridin-3-yl)-4H-1,2,4-triazol-3-amine is used as a building block in the synthesis of agrochemicals, particularly in the development of new pesticides and herbicides. Its antimicrobial properties can be harnessed to protect crops from various pathogens, while its structural features can be modified to target specific pests or weeds, enhancing the effectiveness and selectivity of agrochemicals.
Used in Medicinal Chemistry Research:
5-(Pyridin-3-yl)-4H-1,2,4-triazol-3-amine is used as a valuable precursor in medicinal chemistry research for the exploration of its potential biological activities. Its unique combination of triazole and pyridine rings provides a foundation for the design and synthesis of novel compounds with improved pharmacological properties, such as enhanced potency, selectivity, and reduced side effects.
Used in Drug Discovery and Development:
5-(Pyridin-3-yl)-4H-1,2,4-triazol-3-amine is used as a starting material in drug discovery and development processes. Its versatile properties and structural features allow for the creation of diverse chemical libraries, which can be screened for potential drug candidates with desired therapeutic effects. 5-(Pyridin-3-yl)-4H-1,2,4-triazol-3-amine serves as a valuable tool in the identification and optimization of new drugs for various medical conditions.
Used in Chemical Synthesis:
5-(Pyridin-3-yl)-4H-1,2,4-triazol-3-amine is used as a versatile building block in chemical synthesis, particularly in the preparation of complex organic molecules and heterocycles. Its unique structural features enable the formation of various chemical bonds and functional groups, facilitating the synthesis of a wide range of compounds with diverse applications in pharmaceuticals, agrochemicals, and other industries.

InChI:InChI=1/C7H7N5/c8-7-10-6(11-12-7)5-2-1-3-9-4-5/h1-4H,(H3,8,10,11,12)

Upstream product

• 59-67-6 nicotinic acid 
• 10400-19-8 3-pyridinecarbonyl chloride 
• 46189-75-7 Nicotinic acid diaminomethylene-hydrazide 
• 46189-75-7 nicotinoylaminoguanidine 
• 2834-84-6 aminoguanidine sulphate 
• 1354647-04-3 5-amino-3-(pyridin-3-yl)-1,2,4-triazole hydrochloride 
• 1068-42-4 aminoguanidine sulfate 
• 553-53-7 Nicotinic acid hydrazide 
• 14527-26-5 2-methylisothiourea sulphate 
• 1937-19-5 1-aminoguanidine hydrochloride 
• 10035-10-6 hydrogen bromide 

Downstream Products

• 1338358-62-5 C₁₅H₁₅N₅ 
• 1338351-27-1 N-[(4-fluorophenyl)methyl]-3-(pyridin-3-yl)-1H-1,2,4-triazol-5-amine 
• 1338351-41-9 N-(2-fluorophenyl)-5-[(4-fluorophenyl)methyl]amino-3-(pyridin-3-yl)-1H-1,2,4-triazole-1-carboxamide 
• 1338351-42-0 5-[(4-fluorophenyl)methyl]amino-N-methyl-3-(pyridin-3-yl)-1H-1,2,4-triazole-1-carboxamide 
• 1338351-44-2 2-(5-[(4-fluorophenyl)methyl]amino-3-(pyridin-3-yl)-1H-1,2,4-triazol-1-yl)-1-phenylethan-1-one 
• 122484-49-5 [2-(3,4-Dimethoxy-phenyl)-ethyl]-(5-methyl-2-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine 
• 122484-43-9 7-methyl-2-(3-pyridyl)-5-(3-trifluoromethylphenylamino)-1,2,4-triazolo<1,5-a>pyrimidine 
• 122484-48-4 (3,4-Dichloro-benzyl)-(5-methyl-2-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine 

Relevant academic research and scientific papers

An aqueous medium synthesis and tautomerism study of 3(5)-amino-1,2,4-triazoles

A catalyst-free highly efficient synthesis of 3(5)-amino-5(3)-(het)aryl-1,2,4-triazoles in aqueous medium was performed using conventional heating and microwave irradiation. The tautomerism in the products was investigated using NMR spectroscopy and X-ray crystallography. The effects of the substitution, temperature, solvents, and concentration on the tautomerism were studied. The triazoles were found to exist in 1H-forms, the 4H-form was not observed either in solid state or in solution. In general, 5-amino-1,2,4-triazoles were electronically preferred in the tautomeric equilibrium, but some exceptions from the established relationship were also identified.

Microscale Parallel Synthesis of Acylated Aminotriazoles Enabling the Development of Factor XIIa and Thrombin Inhibitors

Herein we report a microscale parallel synthetic approach allowing for rapid access to libraries of N-acylated aminotriazoles and screening of their inhibitory activity against factor XIIa (FXIIa) and thrombin, which are targets for antithrombotic drugs. This approach, in combination with post-screening structure optimization, yielded a potent 7 nM inhibitor of FXIIa and a 25 nM thrombin inhibitor; both compounds showed no inhibition of the other tested serine proteases. Selected N-acylated aminotriazoles exhibited anticoagulant properties in vitro influencing the intrinsic blood coagulation pathway, but not extrinsic coagulation. Mechanistic studies of FXIIa inhibition suggested that synthesized N-acylated aminotriazoles are covalent inhibitors of FXIIa. These synthesized compounds may serve as a promising starting point for the development of novel antithrombotic drugs.

Acylated 1 H-1,2,4-Triazol-5-Amines Targeting Human Coagulation Factor XIIa and Thrombin: Conventional and Microscale Synthesis, Anticoagulant Properties, and Mechanism of Action

We herein report the conventional and microscale parallel synthesis of selective inhibitors of human blood coagulation factor XIIa and thrombin exhibiting a 1,2,4-Triazol-5-Amine scaffold. Structural variations of this scaffold allowed identifying derivative 21i, a potent 29 nM inhibitor of FXIIa, with improved selectivity over other tested serine proteases and also finding compound 21m with 27 nM inhibitory activity toward thrombin. For the first time, acylated 1,2,4-Triazol-5-Amines were proved to have anticoagulant properties and the ability to affect thrombin-And cancer-cell-induced platelet aggregation. Performed mass spectrometric analysis and molecular modeling allowed us to discover previously unknown interactions between the synthesized inhibitors and the active site of FXIIa, which uncovered the mechanistic details of FXIIa inhibition. Synthesized compounds represent a promising starting point for the development of novel antithrombotic drugs or chemical tools for studying the role of FXIIa and thrombin in physiological and pathological processes.

3-Aryl/Heteroaryl-5-amino-1-(3′,4′,5′-trimethoxybenzoyl)-1,2,4-triazoles as antimicrotubule agents. Design, synthesis, antiproliferative activity and inhibition of tubulin polymerization

Many natural and synthetic substances are known to interfere with the dynamic assembly of tubulin, preventing the formation of microtubules. In our search for potent and selective antitumor agents, a novel series of 1-(3′,4′,5′-trimethoxybenzoyl)-5-amino-1,2,4-triazoles were synthesized. The compounds had different heterocycles, including thiophene, furan or the three isomeric pyridines, and they possessed a phenyl ring bearing electron-releasing or electron-withdrawing substituents at the 3-position of the 5-amino-1,2,4-triazole system. Most of the twenty-two tested compounds showed moderate to potent antiproliferative activities against a panel of solid tumor and leukemic cell lines, with four (5j, 5k, 5o and 5p) showing strong antiproliferative activity (IC50 50 values 2-100-fold lower for Jurkat and RS4;11 cells than those for the three lines derived from solid tumors (HeLa, HT-29 and MCF-7 cells). Compound 5k strongly inhibited tubulin assembly, with an IC50 value of 0.66 μM, half that obtained in simultaneous experiments with CA-4 (IC50 = 1.3 μM).

MULTISUBSTITUTED AROMATIC COMPOUNDS AS INHIBITORS OF THROMBIN

There are provided inter alia multisubstituted aromatic compounds useful for the inhibition of thrombin, which compounds include substituted pyrazolyl or substituted triazolyl. There are additionally provided pharmaceutical compositions. There are additionally provided methods of treating and preventing a disease or disorder, which disease or disorder is amenable to treatment or prevention by the inhibition of thrombin.

Synthesis and structure activity relationship investigation of triazolo[1,5-a]pyrimidines as CB2 cannabinoid receptor inverse agonists

CB2 cannabinoid receptor ligands are known to be therapeutically important for the treatment of numerous diseases. Recently, we have identified the heteroaryl-4-oxopyridine/7-oxopyrimidine derivatives as highly potent and selective CB2 receptor ligands, showing that the pharmakodynamics of the new compounds was controlled by the nature of the heterocycle core. In this paper we describe the synthesis and biological evaluation of 7-oxo-4-pentyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide derivatives that led to the identification of novel CB2 receptor inverse agonists. Cyclic AMP experiments on CB2 receptors expressed in CHO cells revealed that introduction of structural modifications at position 2 of triazolopyrimidine template changes the functional activity from partial to inverse agonism. The molecular docking analysis of the novel structures is reported.

MULTISUBSTITUTED AROMATIC COMPOUNDS AS SERINE PROTEASE INHIBITORS

There are provided inter alia multisubstituted aromatic compounds useful for the inhibition of kallikrein, which compounds include substituted pyrazolyl or substituted triazolyl. There are additionally provided pharmaceutical compositions. There are additionally provided methods of treating and preventing certain diseases or disorders, which disease or disorder is amenable to treatment or prevention by the inhibition of kallikrein.

Synthesis of 3-pyridyl-substituted 5-amino-1,2,4-triazoles from aminoguanidine and pyridinecarboxylic acids

Effect of the molar ratio between reagents, temperature, and synthesis duration on the yield of 3-pyridylsubstituted 5-amino-1,2,4-triazoles in the reaction of aminoguanidine hydrochloride with pyridinecarboxylic acids under acid catalysis conditions was studied. A single-reactor method for synthesis of 3-pyridyl-substituted 5-amino-1,2,4-triazoles and their hydrochlorides was developed.

MULTISUBSTITUTED AROMATIC COMPOUNDS AS INHIBITORS OF THROMBIN

There are provided inter alia multisubstituted aromatic compounds useful for the inhibition of thrombin, which compounds include substituted pyrazolyl or substituted triazolyl. There are additionally provided pharmaceutical compositions. There are additionally provided methods of treating and preventing a disease or disorder, which disease or disorder is amenable to treatment or prevention by the inhibition of thrombin.

7-(3',4'-DIALKOXYPHENYL)-[1,2,4]-TRIAZOLO[1,5-A]PYRIMIDINE COMPOUNDS, PROCESS FOR PREPARING THEREOF, AND PHARMACEUTICAL COMPOSITION FOR TREATING OR PREVENTING ASTHMA, CHRONIC OBSTRUCTIVE PULMONARY DISEASE, ARTHRITIS, ATOPIC DERMATITIS, TUMOR AND DEGENERATIVE BRAIN DISEASES COMPRISING THE SAME

The present invention relates to novel {7-(3',4'-dialkoxyphenyl)-[1,2,4]-triazolo[1,5-a]pyrimidine compounds or pharmaceutically acceptable salts thereof, a process for preparing the same, and pharmaceutical compositions for treating or preventing inflammatory diseases including asthma and chronic obstructive pulmonary disease, arthritis, atopic dermatitis, cancers including leukemia, and degenerative brain diseases including Alzheimer's disease, depression and memory impairment, which comprises the same as an active ingredient.