125866-62-8

Basic information

• Product Name: 4-AMINO-5-(3,4-DIMETHOXY-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL
• Synonyms: 3H-1,2,4-Triazole-3-thione,4-aMino-5-(3,4-diMethoxyphenyl)-2,4-dihydro-;4-amino-5-(3,4-dimethoxyphenyl)-2H-1,2,4-triazole-3-thione;BIM-0036068.P001;CBMicro_036159;ZERO/009889;ZINC00407310;4-Amino-5-(3,4-dimethoxy-phenyl)-2,4-dihydro-3H-1,2,4-Triazol-3-thione
• CAS NO: 125866-62-8
• Molecular Formula: C₁₀H₁₂N₄O₂S
• Molecular Weight: 252.3
• Mol File: 125866-62-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 212 °C(Solv: ethanol (64-17-5))
• Boiling Point: 377.4°Cat760mmHg
• Flash Point: 182°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 6.79E-06mmHg at 25°C
• Refractive Index: 1.675
• PKA: 8.19±0.20(Predicted)
• CAS DataBase Reference: 4-AMINO-5-(3,4-DIMETHOXY-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-5-(3,4-DIMETHOXY-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL(125866-62-8)
• EPA Substance Registry System: 4-AMINO-5-(3,4-DIMETHOXY-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL(125866-62-8)

Safety Data

• Hazardous Substances Data: 125866-62-8(Hazardous Substances Data)

Usage

General Description

4-AMINO-5-(3,4-DIMETHOXY-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL is a chemical compound that belongs to the triazole family. Its molecular structure consists of a triazole ring with an amino group and a thiolic sulfur atom. The compound also contains a substituted phenyl group with two methoxy groups attached to it. This chemical has potential applications in the pharmaceutical and agricultural industries due to its diverse biological activities, including antimicrobial, antifungal, and antitumor properties. Further research and development of this compound may lead to the discovery of new drugs and agrochemicals for various medical and agricultural purposes.

InChI:InChI=1/C10H12N4O2S/c1-15-7-4-3-6(5-8(7)16-2)9-12-13-10(17)14(9)11/h3-5H,11H2,1-2H3,(H,13,17)

Upstream product

• 93-07-2 Veratric acid 
• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 41764-74-3 3,4-dimethoxybenzohydrazide 
• 23269-91-2 5?(3,4?dimethoxyphenyl)?1,3,4?oxadiazole?2?thiol 
• 915101-53-0 C₁₀H₁₁N₂O₃S₂^(1-)*K⁽¹⁺⁾ 
• 23269-91-2 5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3H)-thione 

Downstream Products

• 125866-68-4 5-(3,4-Dimethoxy-phenyl)-4-{[1-thiophen-2-yl-meth-(E)-ylidene]-amino}-4H-[1,2,4]triazole-3-thiol 
• 922681-50-3 C₁₉H₁₈N₄O₃S 
• 840483-79-6 C₂₀H₂₀N₄O₄S 
• 922681-39-8 3-(3,4-dimethoxyphenyl)-6-(2,4-dimethoxyphenyl)-7H-[1,2,4]-triazolo-[3,4-b]-[1,3,4]-thiadiazine 
• 1013750-80-5 C₂₀H₂₀N₄O₄S 
• 922579-37-1 C₁₉H₁₈N₄O₃S 
• 585550-28-3 C₁₉H₁₈N₄O₃S 
• 129081-88-5 3-(3,4-Dimethoxyphenyl)-6-(4-dimethylaminophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 129081-87-4 3-(3,4-Dimethoxy-phenyl)-6-(4-methoxy-phenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 125866-74-2 6-(4-Chloro-phenyl)-3-(3,4-dimethoxy-phenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 129081-86-3 3-(3,4-Dimethoxy-phenyl)-6-(4-fluoro-phenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 129081-89-6 3-(3,4-Dimethoxy-phenyl)-6-thiophen-2-yl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 129081-85-2 5-(3,4-Dimethoxy-phenyl)-4-{[1-(4-dimethylamino-phenyl)-meth-(E)-ylidene]-amino}-4H-[1,2,4]triazole-3-thiol 
• 125866-67-3 5-(3,4-Dimethoxy-phenyl)-4-{[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amino}-4H-[1,2,4]triazole-3-thiol 

Relevant articles and documents

Development of triazolothiadiazine derivatives as highly potent tubulin polymerization inhibitors: Structure-activity relationship, in vitro and in vivo study

Based on our prior work, we reported the design, synthesis, and biological evaluation of fifty-two new triazolothiadiazine-based analogues of CA-4 and their preliminary structure-activity relationship. Among synthesized compounds, Iab was found to be the most potent derivative possessing IC50 values ranging from single-to double-digit nanomolar in vitro, and also exhibited excellent selectivity over the normal human embryonic kidney HEK-293 cells (IC50 > 100 μM). Further mechanistic studies revealed that Iab significantly blocked tubulin polymerization and disrupted the intracellular microtubule network of A549 cells. Moreover, Iab induced G2/M cell cycle arrest by regulation of p-cdc2 and cyclin B1 expressions, and caused cell apoptosis through up-regulating cleaved PARP and cleaved caspase-3 expressions, and down-regulating of Bcl-2. Importantly, in vivo, Iab effectively suppressed tumor growth of A549 lung cancers in a xenograft mouse model without obvious signs of toxicity, confirming its potential as a promising candidate for cancer treatment.

Design, synthesis and bioevaluation of antitubulin agents carrying diaryl-5,5-fused-heterocycle scaffold

A series of 3,6-diaryl-1H-pyrazolo[5,1-c][1,2,4]triazoles (I) and 3,6-diaryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles (II) as antitubulin agents were designed, synthesized and bioevaluated. Compounds (II) 4a, 4d, 4f, 4j, 4l and 4n showed potent antiproli

Identification of a potent new chemotype for the selective inhibition of PDE4

A series of substituted 3,6-diphenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines were prepared and analyzed as inhibitors of phosphodiesterase 4 (PDE4). Synthesis, structure-activity relationships, and the selectivity of a highly potent analogue against related phosphodiesterase isoforms are presented.