87239-96-1

Basic information

• Product Name: 4-AMINO-5-(3-BROMOPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL
• Synonyms: 4-amino-5-(3-bromophenyl)-2H-1,2,4-triazole-3-thione
• CAS NO: 87239-96-1
• Molecular Formula: C₈H₇BrN₄S
• Molecular Weight: 271.137
• Mol File: 87239-96-1.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 365.6 °C at 760 mmHg
• Flash Point: 174.9 °C
• Appearance: /
• Density: 1.9 g/cm³
• Vapor Pressure: 1.55E-05mmHg at 25°C
• Refractive Index: 1.803
• CAS DataBase Reference: 4-AMINO-5-(3-BROMOPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-5-(3-BROMOPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(87239-96-1)
• EPA Substance Registry System: 4-AMINO-5-(3-BROMOPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(87239-96-1)

Safety Data

• Hazardous Substances Data: 87239-96-1(Hazardous Substances Data)

Usage

General Description

4-AMINO-5-(3-BROMOPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL is a chemical compound with a molecular formula C8H6BrN5S. It is a thiol derivative of the triazole compound, and its structure includes an amino group, a bromophenyl group, and a thiol group attached to a triazole ring. 4-AMINO-5-(3-BROMOPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL has potential applications in pharmaceuticals and agrochemicals due to its diverse biological activities, including antibacterial, antifungal, and antitumor properties. It is also used in the synthesis of various pharmaceutical compounds and as a building block in organic chemistry. Additionally, it has been studied for its potential role in chemical sensors and as a ligand for metal complexes in coordination chemistry.

InChI:InChI=1/C8H7BrN4S/c9-6-3-1-2-5(4-6)7-11-12-8(14)13(7)10/h1-4H,10H2,(H,12,14)

Upstream product

• 24398-88-7 ethyl 3-bromobenzoate 
• 585-76-2 m-bromobenzoic acid 
• 2231-57-4 Thiocarbohydrazide 
• 39115-96-3 3-bromo-benzoic acid hydrazide 
• 618-89-3 methyl 3-bromobenzoate 
• 75-15-0 carbon disulfide 
• 87239-93-8 C₈H₆BrN₂OS₂^(1-)*K⁽¹⁺⁾ 
• 203268-69-3 5-(3-Bromo-phenyl)-3H-[1,3,4]oxadiazole-2-thione 
• 1711-09-7 3-bromobenzoyl chloride 

Downstream Products

• 947857-44-5 3-(3-bromophenyl)-6-(3,4-dichlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 1427500-98-8 3-(3-bromophenyl)-6-(furan-3-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 947921-72-4 3-(3-bromophenyl)-6-(pyridin-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 874466-73-6 3-(3-bromophenyl)-6-(pyridin-4-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 1427468-57-2 3-(3-bromophenyl)-6-(3,5-difluoropyridin-2-yl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 947064-13-3 3-(3-bromophenyl)-6-(thiophen-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 1427468-60-7 3-(3-bromophenyl)-6-(thiophen-2-ylmethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 307325-47-9 3-(3-bromophenyl)-6-(4-nitrophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 

Relevant articles and documents

New heparanase-inhibiting triazolo-thiadiazoles attenuate primary tumor growth and metastasis

Compelling evidence ties heparanase, an endoglycosidase that cleaves heparan sulfate side (HS) chains of proteoglycans, with all steps of tumor development, including tumor initiation, angiogenesis, growth, metastasis, and chemoresistance. Moreover, heparanase levels correlate with shorter postoperative survival of cancer patients, encouraging the development of heparanase inhibitors as anti-cancer drugs. Heparanase-inhibiting heparin/heparan sulfate-mimicking compounds and neutralizing antibodies are highly effective in animal models of cancer progression, yet none of the compounds reached the stage of approval for clinical use. The present study focused on newly synthesized triazolo–thiadiazoles, of which compound 4-iodo-2-(3-(p-tolyl)-[1,2,4]triazolo[3,4b][1,3,4]thiadiazol-6-yl)phenol (4-MMI) was identified as a potent inhibitor of heparanase enzymatic activity, cell invasion, experimental metastasis, and tumor growth in mouse models. To the best of our knowledge, this is the first report showing a marked decrease in primary tumor growth in mice treated with small molecules that inhibit heparanase enzymatic activity. This result encourages the optimization of 4-MMI for preclinical and clinical studies primarily in cancer but also other indications (i.e., colitis, pancreatitis, diabetic nephropathy, tissue fibrosis) involving heparanase, including viral infection and COVID-19.

Facile synthesis, biological evaluation and molecular docking studies of novel substituted azole derivatives

In this study, we synthesized the series of novel azole derivatives and evaluated for enzyme inhibition assays, corresponding kinetic analysis and molecular modeling. Among the investigated bioassays, the oxadiazole derivatives 4a-k were found potent α-glucosidase inhibitors while the Schiff base derivatives 7a-k exhibited considerable potential toward urease inhibition. The inhibition kinetics for the most active compounds were analyzed by the Lineweaver–Burk plots to investigate the possible binding modes of the synthesized compounds toward the tested proteins. Moreover, the detailed docking studies were performed on the synthesized library of 4a-k and 7a-k to study the molecular interaction and binding mode in the active site of the modeled yeast α-glucosidase and Jack Bean Urease, respectively. It could be inferred from docking results that theoretical studies are in close agreement to that of the experimental results. The structure of one of the compound 7k was characterized by the single crystal X-ray diffraction analysis in order to find out the predominant conformation of the molecules.

Synthesis of Triazole Based Novel Ionic Liquids and Salts

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