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Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-5-PYRIDIN-3-YL-4H-[1,2,4]TRIAZOLE-3-THIOL is used as a chelating agent for the development of pharmaceutical compounds, leveraging its ability to form coordination complexes with metal ions. This property can enhance the stability and effectiveness of certain drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 4-AMINO-5-PYRIDIN-3-YL-4H-[1,2,4]TRIAZOLE-3-THIOL is utilized as a component in the formulation of pesticides and fungicides, capitalizing on its antimicrobial and antifungal properties to protect crops from various pathogens.
Used as a Corrosion Inhibitor:
4-AMINO-5-PYRIDIN-3-YL-4H-[1,2,4]TRIAZOLE-3-THIOL is employed as a corrosion inhibitor in industrial applications, where its chelating ability helps to prevent the degradation of metal surfaces, thus extending the lifespan of equipment and structures.
Used in Material Science:
4-AMINO-5-PYRIDIN-3-YL-4H-[1,2,4]TRIAZOLE-3-THIOL is used in the development of new materials, potentially enhancing their properties through its incorporation into their molecular structure, which can lead to improved performance characteristics.
Used as a Fluorescent Probe in Bioimaging:
4-AMINO-5-PYRIDIN-3-YL-4H-[1,2,4]TRIAZOLE-3-THIOL is utilized as a fluorescent probe in bioimaging applications, where its optical properties allow for the visualization and tracking of biological processes at the molecular level.

InChI:InChI=1/C7H7N5S/c8-12-6(10-11-7(12)13)5-2-1-3-9-4-5/h1-4H,8H2,(H,11,13)

Upstream product

• 75-15-0 carbon disulfide 
• 553-53-7 Nicotinic acid hydrazide 
• 88317-41-3 potassium N-(pyridine-4-carbonyl)-hydrazine carbodithiolate 
• 3690-46-8 5-(pyridin-3''-yl)-1,3,4-oxadiazole-2(3H)-thione 
• 59-67-6 nicotinic acid 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 3690-46-8 5-(3-pyridinyl)-1,3,4-oxadiazol-2-thiol 

Downstream Products

• 89814-05-1 4-{[(E)-3-Mercapto-5-pyridin-3-yl-[1,2,4]triazol-4-ylimino]-methyl}-phenol 
• 89814-03-9 4-[(E)-3-Phenyl-prop-2-en-(Z)-ylideneamino]-5-pyridin-3-yl-4H-[1,2,4]triazole-3-thiol 
• 89814-09-5 4-{[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-amino}-5-pyridin-3-yl-4H-[1,2,4]triazole-3-thiol 
• 882687-75-4 7-bromo-naphtho[1,2-b]pyran-4-one 
• 332943-03-0 5-(benzylthio)-3-(3-pyridyl)-4-amino-1,2,4-triazole 
• 853891-71-1 4-(pyridine-3-yl)-7-(pyridine-4-yl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole 
• 1021323-90-9 4-(4-chlorobenzylideneamino)-5-(pyridin-3-yl)-2,4-dihydro-[1,2,4]-triazole-3-thione 
• 1021323-88-5 4-(4-methoxybenzylideneamino)-5-(pyridin-3-yl)-2,4-dihydro-[1,2,4]-triazole-3-thione 

Relevant academic research and scientific papers

An extensive research on aldose reductase inhibitory effects of new 4H-1,2,4-triazole derivatives

Aldose reductase (AR) is a key enzyme, which triggers the excessive accumulation of sorbitol in insulin independent tissues leading to severe diabetes-induced microvascular complications. Substantial evidence has proven that AR inhibition is a well-establ

Synthesis, structural, spectroscopic, and thermal studies of some transition-metal complexes of a ligand containing the amino mercapto triazole moiety

A new series of transition-metal complexes of Schiff base ligand containing the amino mercapto triazole moiety (HL) was prepared. The Schiff base and its metal complexes were elucidated by different spectroscopic techniques (infrared [IR], 1H nuclear magnetic resonance, UV–Visible, mass, and electron spin resonance [ESR]), and magnetic moment and thermal studies. Quantum chemical calculations have been carried out to study the structure of the ligand and some of its complexes. The IR spectra showed that the ligand is chelated with the metal ion in a neutral, tridentate, and bidentate manner using NOS and NO donors in complexes 1–6, 10–12, and 7 and 8, respectively, whereas it behaves in a monobasic tridentate fashion using NOS donor sites in copper(II) nitrate complex (9). The magnetic moment and electronic spectra data revealed octahedral and square pyramidal geometries for complexes 2, 11, 12, and 5–8 and 10, respectively. However, the other complexes were found to have tetrahedral (4), trigonal bipyramidal (1 and 3), and square planar (9) structures. Thermal studies revealed that the chelates with different crystallized solvents undergo different types of interactions and the decomposition pathway ended with the formation of metal oxygen (MO) and metal sulfur (MS) as final products. The ESR spectrum of copper(II) complex 10 is axial in nature with hyperfine splitting with 2B1g as a ground state. By contrast, complexes 7 and 8 undergo distortion around the Cu(II) center, affording rhombic ESR spectra. The HL ligand and some of its complexes were screened against two bacterial species. Data showed that complex 12 demonstrated a better antibacterial activity than HL ligand and other chelates.

Synthesis and biological evaluation of novel glycosyl-containing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives as acetylcholinesterase inhibitors

An efficient protocol for the synthesis of novel glycosyl-containing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives starting from the commercially available d-glucosamine hydrochloride is described by reaction of glycosyl isothiocyanate with various aminotriazoles in DMF. Glycosyl isothiocyanate is an important intermediate and synthetic methods are discussed. The acetylcholinesterase inhibitory activity of these compounds was tested by Ellman’s method. It was found that most compounds exhibited over 90% inhibition and they were subsequently evaluated for their IC50values.

Exploiting the Role of Molecular Electrostatic Potential, Deformation Density, Topology, and Energetics in the Characterization of S?N and Cl?N Supramolecular Motifs in Crystalline Triazolothiadiazoles

A detailed analysis of the molecular and crystal packing of a series of pharmaceutically active triazolothiadiazole derivatives is reported. The most notable feature from the analysis of the supramolecular motifs is the presence of inversion dimers due to the formation of strong S?N chalcogen bonds. This has been unequivocally established via inputs from energy calculations from PIXEL, the topological analysis using the approach of QTAIM from AIMALL, an analysis of the molecular electrostatic potentials plotted on Hirshfeld surfaces, and the analysis of the 3D-deformation densities obtained using Crystal Explorer. The total interaction energy for this contact is in the range of 28-33 kJ/mol in the molecules under investigation, and the electrostatic (Coulombic + polarization) contribution toward the total stabilization energy is more than 70%, indicating that such interactions are principally electrostatic in origin. The results from the analysis of the molecular ESP depict that this interaction exists between a strongly electropositive σ-hole on the sulfur atom and an electronegative region on the nitrogen. 3D-deformation density (DD) maps reveal the presence of a charge depletion (CD) region on the sulfur atom which is directed toward the charge concentration (CC) region on the nitrogen atom facilitating formation of such contacts in the crystal. These are further invesigated by QTAIM based calculations which establish the closed-shell nature of these contacts. The crystal packing is further stabilized by the presence of significantly important π?π stacking interactions, wherein the interaction energies, calculated by the PIXEL method, reveal that some of these interactions in crystals have significant contributions from electrostatic components, with a lesser contribution from dispersion forces that normally dominate such interactions. The existence of a contribution of ～48% from electrostatics between stacked rings owing to their unique electrostatic complementarity is a rare supramolecular feature observed in crystal packing in these solids. In addition, the existence of C-H?O, C-H?N, C-H?F, and Cl?N interactions is also characterized by a significant electrostatic component in their formation in crystals of these compounds.

Synthesis and biological evaluation of new Mannich and Schiff bases containing 1,2,4-triazole and 1,3,4-oxadiazole nucleus

5-(Pyridine-3-yl)-1,3,4-oxadiazole-2-thiole 2, obtaining starting from nicotinic acid hydrazide were converted to the corresponding Mannich bases (3a–c) by the reaction with several heterocyclic amines in the presence of formaldehyde. 1,2,4-Triazole-3-thi

1,2,4-Triazolethione derivative containing (hetero)aryl group and piperazine, and preparation method and application thereof

The invention discloses a 1,2,4-triazolethione derivative containing a (hetero)aryl group and piperazine, and a preparation method and an application thereof. The synthesis method has the advantages of few reaction steps, simple and mild conditions, simple operation and high yield. The derivative has a structural formula represented by general formula I and general formula II, and R, R and R in the general formula I and the general formula II are as defined in claim 1. The above compounds have certain in vitro inhibition activity to cucumber fusarium wilt, Cercospora arachidicola Hori, Macrophoma kawatsukai, Altemaria solani, Fusarium graminearum, Rhizoctonia cerealis and other plant pathogens, and especially have high in vitro inhibition activity on the cucumber fusarium wilt, Cercospora arachidicola Hori, Macrophoma kawatsukai and Rhizoctonia cerealis. The compounds of the general formula I and general formula II simultaneously have rice KARI enzyme in vitro inhibition activity. The derivative is suitable for comprehensive control of fungus damages on various crops.

Polyethylene glycol mediated, one-pot, three-component synthetic protocol for novel 3-[3-substituted-5-mercapto-1,2,4-triazol-4-yl]-spiro-(indan-1′,2-thiazolidin)-4-ones as new class of potential antimicrobial and antitubercular agents

A series of 3-[3-substituted-5-mercapto-1,2,4-triazol-4-yl]-spiro-(indan-1′,2-thiazolidin)-4-ones 2 were designed for the purpose of searching for novel antimicrobial agents and have been synthesized conveniently in a single step with a three-component protocol in polyethylene (400) as green reaction media. Thus, the condensation reaction between indane-1-one; 4-amino-5-mercapto-1,2,4-triazoles and mercaptoacetic acid in polyethylene glycol (400) gave quantitatively and analytically pure titled compounds 2. The structure of synthesized compound 2 is based on spectral (IR, 1H-NMR, and 13C-NMR) as well elemental analyses. These compounds have been screened for their antibacterial, antifungal, and antitubercular activities. Some of them have showed significant inhibition on fungal and bacterial growth and antitubercular activity against Mycobacterium tuberculosis. The compounds 2a, 2d, and 2e display antifungal activity against Candida albicans [minimum inhibitory concentration (MIC) 3.13, 6.25 μg/mL] and antibacterial activity against Streptococcus pneumoniae (MIC 3.13 μg/mL) of the order of standard drugs tested under similar conditions, and compound 2a showed better antitubercular activity than other compounds against M. tuberculosis (H37Rv strain, MIC 12.5 μg/mL).

Synthesis of some 1,2,4-triazoles as potential anti-tubercular agents

A series of 5-(N-substituted carboxamidoethylthio)-3-(3'pyridyl)-4- amino-1,2,4-triazole derivatives 6a-j have been synthesized and evaluated for anti-tubercular activity. They are screened in-vitro at 10μg/mL concentration against Mycobacterium tuberculosis H37RV (ATCC 27294). All the compounds are showing antitubercular activity when compared with the standard drug Amikacin. Compounds 6e and 6h are found active as they displayed IC50 and IC90 values at 100μg/mL.

Syntheses, spectral and structural characterization of Ni(II) complexes of 4-amino-5-phenyl/3-pyridyl/thiophen-2H-1,2,4-triazole-3-thione

New mixed ligand complexes [Ni(aptt)2(en)2] (1), [Ni(apytt)2(en)2]×CHCl3 (2) and [Ni(athtt)2(en)2] (3) with 4-amino-5-phenyl-2H-1,2,4- triazole-3-thione (Haptt), 4-amino-5-(pyridin-3-yl)-4,5-dihydro-3H-1,2,4- triazole-3-thione (Hapytt) and 4-amino-5-thiophen-2H-1,2,4-triazole-3-thione (Hathtt) have been prepared containing en as the secondary ligand. The metal complexes have been characterized with the aid of elemental analyses, IR, magnetic susceptibility and single crystal X-ray data. All the complexes are bonded through two nitrogen atoms of two triazole ligands and four nitrogens of two ethylenediamine and the resulting complexes have distorted octahedral geometry. The triazole ligands behave as uninegative monodentate, bonding through triazole nitrogen due to the hard character of the nickel(II). The complexes contain extended hydrogen bonding providing supramolecular framework. The course of the thermal degradation of complex 2 has been investigated by TG-DTA which suggest the loss of CHCl3 molecule around 200 C and finally a residue of NiS is left behind.

Synthesis and characterization of substituted 1,2,4-triazole and its derivatives

Isoniazid was agitated with potassium hydroxide and carbon disulphide to yield sulphur-potassium salt which on refluxed with hydrazine hydrate/ammonia to give substituted 1,2,4-triazoles. The synthesized compounds have been characterized by spectral and e