64369-18-2

Usage

Uses

Used in Pharmaceutical Applications:
(5Z)-4-amino-5-(4-methyl-1,2,3-thiadiazol-5(2H)-ylidene)-4,5-dihydro-3H-1,2,4-triazole-3-thione is used as a building block for the development of new pharmaceuticals due to its unique structural features and potential reactivity. The presence of the 1,2,3-thiadiazol-5(2H)-ylidene moiety and the functional groups in the molecule make it a promising candidate for the creation of novel bioactive compounds.
Used in Chemical Synthesis:
In the chemical synthesis industry, (5Z)-4-amino-5-(4-methyl-1,2,3-thiadiazol-5(2H)-ylidene)-4,5-dihydro-3H-1,2,4-triazole-3-thione can be utilized as a versatile intermediate for the synthesis of various complex organic compounds. Its functional groups and structural features allow for further modification and incorporation into a wide array of molecules, expanding the scope of chemical products that can be developed.
Used in Research and Development:
(5Z)-4-amino-5-(4-methyl-1,2,3-thiadiazol-5(2H)-ylidene)-4,5-dihydro-3H-1,2,4-triazole-3-thione is also valuable in the field of research and development, where it can be employed to study the properties and reactivity of heterocyclic compounds. Understanding the behavior of (5Z)-4-amino-5-(4-methyl-1,2,3-thiadiazol-5(2H)-ylidene)-4,5-dihydro-3H-1,2,4-triazole-3-thione can contribute to the advancement of organic chemistry and the discovery of new materials and applications.

Upstream product

• 1003849-13-5 4-methyl-1,2,3-thiadiazole-5-carbonyl-2-dithiocarboxylhydrazide, potassium salt 
• 75-15-0 carbon disulfide 
• 75423-15-3 4-methyl-4,5-dihydro-1,2,3-thiadiazole-5-carbohydrazide 
• 64369-44-4 N'-(4-methyl-[1,2,3]thiadiazole-5-carbonyl)-hydrazinecarbodithioic acid methyl ester 

Downstream Products

• 64369-27-3 6-methyl-3-(4-methyl-[1,2,3]thiadiazol-5-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 64369-30-8 3-(4-methyl-[1,2,3]thiadiazol-5-yl)-6-phenyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 64369-31-9 6-benzyl-3-(4-methyl-[1,2,3]thiadiazol-5-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 1204341-35-4 C₁₂H₉FN₆S₂ 
• 1204341-36-5 C₁₂H₉FN₆S₂ 
• 1204341-38-7 C₁₃H₉F₃N₆S₂ 
• 1204341-39-8 C₁₃H₉F₃N₆S₂ 
• 1204341-44-5 C₁₄H₁₂N₆S₂ 
• 1204341-32-1 C₁₃H₁₂N₆OS₂ 
• 1204341-33-2 C₁₃H₁₂N₆OS₂ 
• 1204341-31-0 C₁₃H₁₂N₆OS₂ 
• 1204341-40-1 C₁₂H₉N₇O₂S₂ 
• 1204341-34-3 C₁₂H₉FN₆S₂ 
• 1204341-42-3 C₁₂H₉N₇O₂S₂ 

Relevant academic research and scientific papers

1, 2, 4-triazole [3, 4-b]-1, 3, 4-thiadiazine derivative as well as preparation method and application thereof

The invention provides a triazolothiadiazine derivative as well as a preparation method and application thereof, and particularly relates to a 1, 2, 4-triazole [3, 4-b]-1, 3, 4-thiadiazine derivative of which the chemical structural general formula is shown in a formula VI defined in the description. The invention discloses the structural general formula and a synthesis method of the compound, application of the compound as an insecticide, a bactericide and an anti-plant virus agent, and application and a preparation method of the compound in preventing and treating insect pests, diseases and virus diseases of agricultural, forestry and horticultural plants in combination with agriculturally acceptable auxiliaries or synergists and commercial insecticides, bactericides, plant virus resisting agents and acaricides.

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.

Synthesis, crystal structure, and biological activity of 4-methyl-1,2,3-thiadiazole-containing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles

Heterocyclic compounds play an important role as the main sources of lead molecules of agrochemicals. Synthesis and biological activity of thiadiazole-containing 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazoles were seldom reported. To find novel lead compounds with various biological activities, a series of 6-substituted-3-(4-methyl-1,2,3-thiadiazolyl)[1,2,4]triazolo[3,4-b][1, 3,4]thiadizoles were rationally designed and synthesized according to the principle of combinations of bioactive substructures by the condensation of 3-(4-methyl-1,2,3-thiadiazolyl)-4-amino-1,2,4-triazole-5-thione with various carboxylic acids and phosphorus oxychloride. All newly synthesized compounds were identified by proton nuclear magnetic resonance (1H NMR), infrared spectroscopy (IR), electroionization mass spectrometry (EI/MS), and elementary analysis. The crystal structure of 3-(4-methyl-1,2,3-thiadiazolyl)-6- (4-methylphenyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadizole was determined by X-ray diffraction crystallography. In this crystal, two intermolecular hydrogen bonds (N2- ? -H-C12 and N3... H-C13), a weak intermolecular interaction (S...S), and the weak pπ-pπ intermolecular interaction were observed. Fungicide screening indicated that all of the target compounds showed certain extent of growth inhibition against fungi tested. 3-(4Methyl-1,2,3-thiadiazolyl) -6-n-propyl[1,2,4]triazolo[3,4-6][1,3,4]thiadizole and 3-(4-methyl-1,2,3- thiadiazolyl)-6-trichloromethyl[1,2,4]triazolo[3,4-b][1,3,4]thiadizole were found to have potential wide spectrum of fungicide activity. The median effective concentrations (EC50) detected for 3-(4-methyl-1,2, 3thiadiazolyl)-6-trichloromethyl[1,2,4]triazolo[3,4-b][1,3,4]thiadizole to six fungi were from 7.28 μmol/L against Pelicularia sasakii (Shirai) to 42.49 μmol/L against Alternaria solan!. The results indicated that thiadiazolecontaining 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazoles were potential fungicide lead compounds.

3-ARYL-6-ARYL-7H-[1,2,4]TRIAZOLO[3,4-b][1,3,4]THIADIAZINES AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF

Disclosed are 3-aryl-6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and analogs thereof, represented by the Formula (I), wherein Ar1, Q2, R1, R2, dashed line and X are defined herein. The present invention relates to the discovery that compounds having Formula (I) are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.