39751-84-3

Basic information

• Product Name: 5-(2-BROMO-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL
• Synonyms: 5-(2-bromophenyl)-1,2-dihydro-1,2,4-triazole-3-thione
• CAS NO: 39751-84-3
• Molecular Formula: C₈H₆BrN₃S
• Molecular Weight: 256.1223
• Mol File: 39751-84-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 325.6°Cat760mmHg
• Flash Point: 150.7°C
• Appearance: /
• Density: 1.83g/cm³
• Vapor Pressure: 0.000228mmHg at 25°C
• Refractive Index: 1.775
• CAS DataBase Reference: 5-(2-BROMO-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-BROMO-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL(39751-84-3)
• EPA Substance Registry System: 5-(2-BROMO-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL(39751-84-3)

Safety Data

• Hazardous Substances Data: 39751-84-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H6BrN3S/c9-6-4-2-1-3-5(6)7-10-8(13)12-11-7/h1-4H,(H2,10,11,12,13)

Upstream product

• 88-65-3 2-bromobenzoic-acid 
• 79-19-6 thiosemicarbazide 
• 7154-66-7 2-bromobenzoic acid chloride 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 29418-67-5 2-bromobenzohydrazide 
• 39631-31-7 N¹-(o-bromobenzoyl)-3-thiosemicarbazide 

Downstream Products

• 1276032-82-6 5-o-bromophenyl-3-(β-D-glucopyranosylthio)-1,2,4-triazole 
• 1276032-72-4 5-o-bromophenyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthio)-1,2,4-triazole 
• 114362-04-8 2-(o-bromophenyl)-5-(p-bromophenyl)thiazolo-<3,2-b>-s-triazole 
• 114362-05-9 2-(o-bromophenyl)-5-(p-chlorophenyl)thiazolo-<3,2-b>-s-triazole 
• 114362-06-0 2-(o-bromophenyl)-5-(p-tolyl)thiazolo-<3,2-b>-s-triazole 
• 114362-07-1 2-(o-bromophenyl)-5-phenylthiazolo-<3,2-b>-s-triazole 
• 114361-98-7 5-(p-bromophenacylthio)-3-o-bromophenyl-s-triazole hydrobromide 
• 114361-99-8 5-(p-chlorophenacylthio)-3-o-bromophenyl-s-triazole hydrobromide 
• 114362-00-4 5-(p-methylphenacylthio)-o-bromophenyl-s-triazole hydrobromide 
• 114388-33-9 5-phenacyclthio-3-o-bromophenyl-s-triazole hydrobromide 

Relevant articles and documents

Development of phenyltriazole thiol-based derivatives as highly potent inhibitors of DCN1-UBC12 interaction

Defective in cullin neddylation 1(DCN1) is a co-E3 ligase that is important for cullin neddylation. Dysregulation of DCN1 highly correlates with the development of various cancers. Herein, from the initial high-throughput screening, a novel hit compound 5a containing a phenyltriazole thiol core (IC50 value of 0.95 μM for DCN1-UBC12 interaction) was discovered. Further structure-based optimization leads to the development of SK-464 (IC50 value of 26 nM). We found that SK-464 not only directly bound to DCN1 in vitro, but also engaged cellular DCN1, suppressed the neddylation of cullin3, and hindered the migration and invasion of two DCN1-overexpressed squamous carcinoma cell lines (KYSE70 and H2170). These findings indicate that SK-464 may be a novel lead compound targeting DCN1-UBC12 interaction.

Design, synthesis, and negative inotropic evaluation of 4-phenyl-1H-1,2,4-triazol-5(4H)-one derivatives containing triazole or piperazine moieties

In this study, four novel series of 4-phenyl-1H-1,2,4-triazol-5(4H)-one derivatives containing triazole or piperazine moieties were designed, synthesized, and evaluated for negative inotropic activity by measuring the left atrium stroke volume in isolated rabbit heart preparations. Almost all of the compounds showed an ability to moderate the cardiac workload by decreasing the heart rate and contractility. Among them, 7h was found to be the most potent with a change in stroke volume of ?48.22?±?0.36% at a concentration of 3?×?10?5?mol/L (metoprolol: ?9.74?±?0.14%). The cytotoxicity of these compounds was evaluated using the human cervical cancer cell line HeLa, the liver cancer cell line Hep3B, and the human normal hepatic cell line LO2. A preliminary study of the mechanism of action for the compound 7h on the regulation of atrial dynamics with ATP-sensitive K+ channel and L-type Ca2+ channel blockers glibenclamide and nifedipine was performed in the isolated perfused beating rabbit atria.

Heterocyclic Systems Containing Bridgehead Nitrogen Atom: Part LVII-Syntheses of 2,5-Disubstituted Thiazolo-s-triazoles and 3,5-Disubstituted Thiazolo-s-triazoles

5-Mercapto-3-substituted-s-triazoles (III, R1 = o-MeOC6H4, R1 = o-BrC6H4) on reaction with α-halogenoketones in anhyd. ethanol give ketones (IVa-a2, IVb-b3) which on cyclization with polyphosphoric acid (PPA) furnish the respective thiazolo-s-triaz