117320-66-8

Basic information

• Product Name: 4-AMINO-5-(3-CHLOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL
• Synonyms: 4-amino-5-(3-chlorophenyl)-2H-1,2,4-triazole-3-thione;ZINC03886910
• CAS NO: 117320-66-8
• Molecular Formula: C₈H₇ClN₄S
• Molecular Weight: 226.69
• Mol File: 117320-66-8.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 348.9°Cat760mmHg
• Flash Point: 164.8°C
• Appearance: /
• Density: 1.62g/cm³
• Vapor Pressure: 4.89E-05mmHg at 25°C
• Refractive Index: 1.775
• CAS DataBase Reference: 4-AMINO-5-(3-CHLOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-5-(3-CHLOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(117320-66-8)
• EPA Substance Registry System: 4-AMINO-5-(3-CHLOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(117320-66-8)

Safety Data

• Hazardous Substances Data: 117320-66-8(Hazardous Substances Data)

Usage

General Description

4-AMINO-5-(3-CHLOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL is a chemical compound with the molecular formula C8H6ClN3S. It is a thiol derivative of 1,2,4-triazole and contains an amino group and a chlorophenyl group. 4-AMINO-5-(3-CHLOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL has potential pharmaceutical applications as it exhibits antimicrobial and antifungal properties. It is also used in the synthesis of various biologically active compounds and as a building block in organic synthesis. Additionally, it has been studied for its potential use in corrosion inhibition and as a sensor for metal ions. Overall, 4-AMINO-5-(3-CHLOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL is a versatile compound with a wide range of potential applications in pharmaceutical, chemical, and material science industries.

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

Upstream product

• 75-15-0 carbon disulfide 
• 1673-47-8 3-chlorobenzhydrazide 
• 1128-76-3 3-chloro-benzoic acid ethyl ester 
• 2905-65-9 methyl 3-chlorobenzoate 
• 535-80-8 3-chlorobenzoate 
• 41491-54-7 5-(3'-chlorophenyl)-1,3,4-oxadiazole-2(3H)-thione 

Downstream Products

• 117376-45-1 3-(m-Chlorophenyl)-5H-s-triazolo<3',4':2,3><1,3,4>thiadiazino<5,6-b>quinoxaline 
• 117320-87-3 3-(3-chlorophenyl)-6-(4-nitrophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 117320-88-4 6-Biphenyl-4-yl-3-(3-chloro-phenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 943868-20-0 2-((Z)-{[3-(3-chlorophenyl)-5-thioxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]imino})bezoic acid 
• 943868-21-1 3-(3-chlorophenyl)[1,2,4]triazolo[4',3':4,5][1,3,4]thiadiazolo[2,3-a]isoindol-6(10bH)-one 
• 1085387-50-3 C₂₃H₁₈Cl₂N₈S₂ 
• 1085384-72-0 C₂₅H₂₂Cl₂N₈S₂ 
• 1119751-35-7 1,8-bis[(3-m-chlorophenyl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl]octane 
• 1227681-97-1 C₂₈H₁₄Cl₂N₈S₂ 
• 1251005-98-7 6-(1-adamantyl)-3-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 1293362-50-1 methyl 3-(3-(3-chlorophenyl)-5-thioxo-1H-1,2,4-triazol-4-ylimino)cholanate 
• 1356353-81-5 3-(3-chlorophenyl)-6-(4-chlorophenyl)amino-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole 
• 1356353-83-7 6-(4-bromophenyl)amino-3-(3-chlorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole 
• 1309605-45-5 3,6-bis(3-chlorophenyl)-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.

1,2,4-Triazole-3-thione Compounds as Inhibitors of Dizinc Metallo-β-lactamases

Metallo-β-lactamases (MBLs) cause resistance of Gram-negative bacteria to β-lactam antibiotics and are of serious concern, because they can inactivate the last-resort carbapenems and because MBL inhibitors of clinical value are still lacking. We previously identified the original binding mode of 4-amino-2,4-dihydro-5-(2-methylphenyl)-3H-1,2,4-triazole-3-thione (compound IIIA) within the dizinc active site of the L1 MBL. Herein we present the crystallographic structure of a complex of L1 with the corresponding non-amino compound IIIB (1,2-dihydro-5-(2-methylphenyl)-3H-1,2,4-triazole-3-thione). Unexpectedly, the binding mode of IIIB was similar but reverse to that of IIIA. The 3 D structures suggested that the triazole–thione scaffold was suitable to bind to the catalytic site of dizinc metalloenzymes. On the basis of these results, we synthesized 54 analogues of IIIA or IIIB. Nineteen showed IC50 values in the micromolar range toward at least one of five representative MBLs (i.e., L1, VIM-4, VIM-2, NDM-1, and IMP-1). Five of these exhibited a significant inhibition of at least four enzymes, including NDM-1, VIM-2, and IMP-1. Active compounds mainly featured either halogen or bulky bicyclic aryl substituents. Finally, some compounds were also tested on several microbial dinuclear zinc-dependent hydrolases belonging to the MBL-fold superfamily (i.e., endonucleases and glyoxalase II) to explore their activity toward structurally similar but functionally distinct enzymes. Whereas the bacterial tRNases were not inhibited, the best IC50 values toward plasmodial glyoxalase II were in the 10 μm range.

Synthesis, anti-HIV activity and Molecular modeling study of 3-aryl-6-adamantylmethyl-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazole derivatives

A series of novel 3-aryl-6-adamantylmethyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles 6a-l were synthesized by a simple method with the aim of developing novel HIV non-nucleoside reverse transcriptase inhibitors. All the synthesized compounds were structurally confirmed by spectral analyses. The structure of 6a was unambiguously verified by X-ray structure determination. The synthesized compounds were evaluated for their anti-HIV activity and four analogs displayed moderate inhibitory activity with EC50 values ranging from 10.10 to 12.40 μg mL-1. Molecular docking of 6g with HIV-1 reverse transcriptase was studied to rationalize some structureactivity relationships (SARs).