68468-95-1

Basic information

• Product Name: 4-AMINO-3-(4-CHLOROPHENYL)-5-MERCAPTO-4H-1,2,4-TRIAZOLE
• Synonyms: IFLAB-BB F1219-1414;CHEMBRDG-BB 5710725;BUTTPARK 9\07-03;ASISCHEM D13312;4-AMINO-5-(4-CHLOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL;4-AMINO-3-(4-CHLOROPHENYL)-5-MERCAPTO-4H-1,2,4-TRIAZOLE;4-AMINO-3-MERCAPTO-5-(4-CHLOROPHENYL)-[1,2,4-]TRIAZOLE;AKOS TOT-0034
• CAS NO: 68468-95-1
• Molecular Formula: C₈H₇ClN₄S
• Molecular Weight: 226.69
• Mol File: 68468-95-1.mol
• Article Data: 44

Chemical Properties

• Melting Point: 174-176°C
• Boiling Point: 336.5°Cat760mmHg
• Flash Point: 157.3°C
• Appearance: /
• Density: 1.62g/cm³
• Vapor Pressure: 0.000112mmHg at 25°C
• Refractive Index: 1.775
• CAS DataBase Reference: 4-AMINO-3-(4-CHLOROPHENYL)-5-MERCAPTO-4H-1,2,4-TRIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-3-(4-CHLOROPHENYL)-5-MERCAPTO-4H-1,2,4-TRIAZOLE(68468-95-1)
• EPA Substance Registry System: 4-AMINO-3-(4-CHLOROPHENYL)-5-MERCAPTO-4H-1,2,4-TRIAZOLE(68468-95-1)

Safety Data

• Hazardous Substances Data: 68468-95-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H7ClN4S/c9-6-3-1-5(2-4-6)7-11-12-8(14)13(7)10/h1-4H,10H2,(H,12,14)

Upstream product

• 1126-46-1 Methyl 4-chlorobenzoate 
• 536-40-3 4-chlorobenzoic acid hydrazide 
• 75-15-0 carbon disulfide 
• 2231-57-4 Thiocarbohydrazide 
• 23766-28-1 5-(4-chlorophenyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione 
• 74-11-3 para-chlorobenzoic acid 
• 38539-88-7 potassium p-chlorobenzoylhydrazinodithioformate 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 10364-95-1 1-(4-chloro-benzoyl)-1H-imidazole 
• 96951-77-8 N'-(4-Chloro-benzoyl)-hydrazinecarbodithioic acid 
• 23766-28-1 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-thiol 

Downstream Products

• 87240-01-5 3-(4-Chlorophenyl)-s-triazolo<3,4-b><1,3,4>thiadiazol-6(5H)-thione 
• 139268-00-1 4-<5-(4-p-Chlorophenyl)-2-furfurylidene>amino-3-mercapto-5-p-chlorophenyl-1,2,4-triazole 
• 139268-18-1 6-<5-(4-Chlorophenyl)-2-furyl>-3-p-chlorophenyl-1,2,4-triazolo<3,4-b>-1,3,4-thiadiazole 
• 108222-56-6 3-(4-chlorophenyl)-6-(2-oxochromen-3-yl)-7H[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 113486-87-6 3,6-Di(4-chlorophenyl)-s-triazolo<3,4-b><1,3,4>thiadiazole 
• 113486-94-5 3,3'-Bis-(4-chloro-phenyl)-[6,6']bi[[1,2,4]triazolo[3,4-b][1,3,4]thiadiazolyl] 
• 111828-04-7 (4-amino-5-p-chlorophenyl-4H-1,2,4-triazol-3-ylsulphanyl)-methylenenitrile 
• 136633-12-0 3-(4'-chlorophenyl)-(1:2:4)-triazolo-[3,4-b](1,3,4)thiadiazepino(6,7-3,2)quinoline 

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.

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.

Synthesis and antimicrobial activity of piperine analogues containing 1,2,4-triazole ring

A series 1,2,4-triazole piperine analogues (TP1-TP6) were designed and synthesized. The structures were confirmed using 1H NMR and 13C NMR. Antibacterial study was done using Gram-positive (Staphylococcus aureus and Bacillus cereus) and Gram-negative microorganisms (E. coli and Pseudomonas aeruginosa) by disc diffusion method. Compound containing chloro substitution (TP6) showed the highest effect, while compound TP1, TP3, TP4, TP5 showed the moderate activity.