61019-27-0

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-5-(2-THIENYL)-4H-1,2,4-TRIAZOLE-3-THIOL is used as a key component in the development of antimicrobial and antifungal agents. Its unique structure allows it to target and inhibit the growth of various microorganisms, making it a promising candidate for new therapeutic agents.
Used in Industrial Settings:
4-AMINO-5-(2-THIENYL)-4H-1,2,4-TRIAZOLE-3-THIOL is being researched for its potential use as a corrosion inhibitor. Its ability to form protective layers on metal surfaces can help prevent corrosion and extend the lifespan of industrial equipment, reducing maintenance costs and downtime.
Used in Organic Electronic Devices:
The thienyl group present in 4-AMINO-5-(2-THIENYL)-4H-1,2,4-TRIAZOLE-3-THIOL may impart unique electronic properties to the compound. This makes it of interest for use in organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic solar cells, where its electronic properties can be harnessed to improve device performance and efficiency.

InChI:InChI=1/C6H6N4S2/c7-10-5(8-9-6(10)11)4-2-1-3-12-4/h1-3H,7H2,(H,9,11)

Upstream product

• 75-15-0 carbon disulfide 
• 2361-27-5 2-thienylhydrazide 
• 2810-04-0 Ethyl thiophene-2-carboxylate 
• 41526-38-9 potassium N'-(thiophene-2-carbonyl) hydrazine carbodithioate 
• 527-72-0 2-thiophenylcarboxylic acid 
• 2231-57-4 Thiocarbohydrazide 

Downstream Products

• 80809-42-3 3-(2-thienyl)-6-amino-s-triazolo<3,4-b>-1,3,4-thiadiazole 
• 1622230-06-1 4-[imino-(3-(2-nitrophenyl)-2-ethylenyl)]-3-mercapto-5-(2-thienyl)-4H-1,2,4-triazole 

Relevant academic research and scientific papers

Investigation of the electronic properties of solvents (water, benzene, methanol) using IEFPCM model, spectroscopic investigation with docking and MD simulations of a thiadiazole derivative with anti-tumor activities

6-(4-Chlorophenyl)-3-(thiophen-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]-thiadiazole (CLP) was synthesized and spectroscopic investigations have been made experimentally and theoretically. The electrostatic potential maps showed the reactive sites in CLP compound and its halogenated derivatives. The various chemical descriptors and NLO properties are predicted and compared for CLP with its halogenated derivatives. The stability of CLP was studied with NBO analysis. For diverse solvents (water, benzene, and methanol) and gas phase, UV–vis spectra are being used to assess the electronic transition. Binding affinities with target protein were carried out which gave the effects of bio-efficiency due to the halogen substitution. The binding affinity values were increasing from that of the parent molecule and are high for meta substitutions (with chlorine positional changes). The MD simulations and docking studies suggested inhibitory activity against CDK2 and could be considered as anticancer candidates.

Discovery of Novel Triazolothiadiazines as Fungicidal Leads Targeting Pyruvate Kinase

Pyruvate kinase (PK) was discovered as a potent new target for novel fungicide development. A series of novel triazolothiadiazine derivatives were rationally designed and synthesized by a ring expansion strategy and computer-aided pesticide design using the 3D structure of Rhizoctonia solani PK (RsPK) obtained by homology modeling as a receptor and our previously discovered lead YZK-C22 as a ligand. The in vitro bioassay results indicated that compounds 4g, 6h, 6m, 6n, 6o, and 6p exhibited good activity against R. solani with the EC50 values falling between 10.99 and 72.76 μM. Especially, 6m showed similar potency to YZK-C22 (10.99 vs 11.97 μM of the EC50 value, respectively). The in vivo bioassay results suggested that 6m against R. solani at a concentration of 200 μg/mL displayed a numerically higher inhibition than YZK-C22 (70 vs 60%, respectively). A field experiment validated that 6m at an application rate of 120 g ai/ha showed comparable efficacy against R. solani to thifluzamide at an application rate of 80 g ai/ha (77.80 vs 84.5%, respectively). Enzymatic inhibition suggested that the potency of 6m was about twofold lower than that of YZK-C22 (67.30 vs 32.64 μM of IC50, respectively). Fluorescence quenching studies validated that RsPK was quenched by both 6m and YZK-C22, implying that they both might act at the same target site of PK. A possible binding conformation of 6m in the RsPK active site was depicted by molecular docking. Our studies suggest that 6m could be a fungicidal lead targeting PK.

Copper metal complex and preparation method and application thereof

The invention discloses a copper metal complex and a preparation method and application thereof. The copper metal complex uses a triazole compound or a thiadiazole compound as a ligand, the active properties of copper ions can be played when the complex is coordinate bonding with the copper metal ions, the copper ions deliver the ligand to the key positions of plants or pests so as to effectively remove pathogenic bacteria and the pests, and the target hitting rate and high efficiency of pesticides are improved. The preparation method includes few steps and is simple in operation but is high in yield and productivity, a large amount of time and cost can be saved in actual production, and economic benefits are good. The copper metal complex has the inhibiting effect on growth and proliferation of early disease bacteria of tomatoes, fusarium oxysporum of cucumbers, fusarium oxysporum of bananas and gloeosporium musarum, and can serve as a pesticide intermediate to be applied to preparation and application of different agricultural fungicides.

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.

INHIBITORS OF UDP-GALACTOPYRANOSE MUTASE

Compounds and salts thereof which are acyl-sulfonamides or certain carboxylic acids and which inhibit microbial growth or attenuate the virulence of pathogenic microorganisms and which inhibit UDP-galactopyranose mutase (UGM). Compounds of the invention include 2-aminothiazoles and triazolothiadiazines, particularly 3,6,7-substituted-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines, and 2-amino and salts thereof. Methods for inhibiting growth or attenuating virulence of microbial pathogens including mycobacterium, for example, M. tuberculosis and M. smegmatis and Klebsiella, for example, Klebsiella pneumoniae. Methods for inhibiting eukaryotic human and animal pathogens, and fungi and nematodes in particular. Methods for treatment of infections by prokaryotic and eukaryotic pathogens employing compounds of the invention.

1, 2, 4- triazoles[3, 4-b]-1, 3, 4-thiadiazole derivative containing glucosamine, and preparation method and application thereof

The invention relates to a 1, 2, 4- triazoles[3, 4-b]-1, 3, 4-thiadiazole derivative containing glucosamine. Theinvention also relates to a synthetic method of the 1, 2, 4- triazoles[3, 4-b]-1, 3, 4-thiadiazole derivative containing glucosamine. The method comprises the following steps of: reacting substituted hydrazine with potassium hydroxide and carbon disulfide to obtain potassium salt; conducting cyclization on the potassium salt under the action of hydrazine hydrate to obtain 3-substituted-4-amino-5- sulfydryl-1,2,4-triazole, reacting the 3-substituted-4-amino-5- sulfydryl-1,2,4 -triazole with 2-deoxy-2-isothiocyanate-1,3,4,6-quaternary-O-benzyl-beta-D-glucopyranose for direct synthesis of N- (1,3,4, 6- quaternary-O-benzyl-beta-D-glucopyranose-2-yl) -6-amino-3- substituted-1,2,4-triazole[3,4-b]-1,3,4- thiadiazole. The synthesis method of the invention is simple, has small environmental pollution and simple posttreatment; and the synthesized material has strong inhibiting effect on acetylcholinesterase has broad application prospects in preparing anti-acetylcholinesterase drugs.

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.

Heterocyclic systems containing bridgehead nitrogen atom: Synthesis and bioactivity of 3-(2-thienyl)-s-triazolo[3,4-b][1,3,4]thiadiazole, 2-(2-thienyl)triazolo[3,2-b]-s-triazole and isomeric 3-(2-thienyl)-thiazolo[2,3-c]-s-triazole

The synthesis of 2-(2-thienyl)-5-p-bromophenylthiazolo[3,2-b]-s-triazole 5 has been achieved starting from 5-mercapto-3-(2- thienyl)-s-triazole 3. Compound 3 on condensation with p-bromophenacyl bromide gives the ketone 4 which on cyclization with PPA affords, 5-p-bromophenyl-2-(2-thienyl)thiazolo[3,2-b]s-triazole 5 and not the isomeric 5-(p-bromophenyl)-3-(2-thienyl)thiazolo[2,3-c]-s-triazole 7. This has been established by an unequivocal synthesis of 7 through POCl3 cyclization of 2-thienoylhydrazino-4-p-bromophenyl thiazole hydrobromide 6. However, the condensation of 4-amino-3-(2-thienyl)-5-mercapto-s-triazole 8 with carbon disulphide furnishes 3-(2-thienyl)-striazolo[3,4-b][1,3,4]thiadiazole-6(5H)-thione 9 in one step only. The diuretic, antibacterial and antifungal activities of these compounds have also been evaluated.

Synthesis of some 4-(alkylidene/arylidene)amino-2,4-dihydro-5-(2-thienyl)-3H-1,2,4- triazole-3-thiones tested for antimicrobial activity

A series of 4-(alkylidene/arylidene)amino-2,4-dihydro-5-(2-thienyl)-3H-1,2,4- triazole-3-thiones (2a-h) were synthesized. The structural elucidation of all the compounds was made on the basis of analytical and spectral data (IR, 1H-NMR and EIMS). All synthesized compounds were evaluated for in vitro antimicrobial activity against various bacteria and fungi. Some of the compounds demonstrated antimicrobial activity against Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, Trichophyton rubrum, Trichophyton mentagrophytes var. erinacei NCPF-375 and Microsporum canis (MIC 50-6.25 mg/ml). The in vitro antimycobacterial activity of the new compounds was also investigated. Some of the compounds showed varying degrees of inhibition (2-40%) against Mycobacterium tuberculosis H37Rv in the primary screen that was conducted at 12.5 mg/ml using the BACTEC 460 radiometric system.