36209-49-1

Basic information

• Product Name: 4-AMINO-5-(4-METHOXY-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL
• Synonyms: 4-amino-5-(4-methoxyphenyl)-2H-1,2,4-triazole-3-thione
• CAS NO: 36209-49-1
• Molecular Formula: C₉H₁₀N₄OS
• Molecular Weight: 222.27
• Mol File: 36209-49-1.mol
• Article Data: 40

Chemical Properties

• Boiling Point: 348°Cat760mmHg
• Flash Point: 164.2°C
• Appearance: /
• Density: 1.46g/cm³
• Vapor Pressure: 5.2E-05mmHg at 25°C
• Refractive Index: 1.711
• CAS DataBase Reference: 4-AMINO-5-(4-METHOXY-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-5-(4-METHOXY-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL(36209-49-1)
• EPA Substance Registry System: 4-AMINO-5-(4-METHOXY-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL(36209-49-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 36209-49-1(Hazardous Substances Data)

Usage

General Description

The chemical 4-AMINO-5-(4-METHOXY-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL, also known as AMPT, is a sulfur-containing heterocyclic compound with potential anticancer and antitumor properties. It is a member of the 1,2,4-triazole family and contains a thiol group. AMPT has been studied for its ability to inhibit the enzyme thymidylate synthase, which is important for DNA synthesis and repair. This inhibition can lead to the suppression of tumor cell growth, making it a potential candidate for cancer treatment. Additionally, AMPT has shown activity in inducing apoptosis (programmed cell death) in cancer cells, further supporting its potential as a therapeutic agent.

InChI:InChI=1/C9H10N4OS/c1-14-7-4-2-6(3-5-7)8-11-12-9(15)13(8)10/h2-5H,10H2,1H3,(H,12,15)

Upstream product

• 121-98-2 methyl 4-methoxybenzoate 
• 2231-57-4 Thiocarbohydrazide 
• 75-15-0 carbon disulfide 
• 3290-99-1 4-methoxybenzoic acid hydrazide 
• 94-30-4 ethyl 4-methoxybenzoate 
• 100-09-4 4-methoxybenzoic acid 
• 10364-93-9 1-(4-methoxybenzoyl)-imidazole 
• 83511-12-0 acetic p-anisic anhydride 
• 23766-26-9 5?(4?methoxyphenyl)?1,3,4?oxadiazole?2?thiol 
• 85103-41-9 potassium N-(4-methoxybenzoyl)hydrazinecarbodithioate 
• 100-07-2 4-methoxy-benzoyl chloride 
• 451-82-1 (2-fluorophenyl)acetic acid 
• 116622-94-7 2-(2-fluorophenyl)acetohydrazide 
• 57486-67-6 methyl o-fluorophenylacetate 

Downstream Products

• 113486-93-4 6,6'-Bis<3-(4-methoxyphenyl)-s-triazolo<3,4-b><1,3,4>thiadiazole> 
• 13228-89-2 3-(4-Methoxyphenyl)-s-triazolo<3,4-b><1,3,4>thiadiazol-6(5H)-thione 
• 3176-54-3 6-Amino-3-(4-methoxyphenyl)-s-triazolo<3,4-b><1,3,4>thiadiazole 
• 113486-85-4 6-(4-Chlorophenyl)-3-(methoxyphenyl)-s-triazolo<3,4-b><1,3,4>thiadiazole 
• 221009-64-9 3-[(Z)-3-Mercapto-5-(4-methoxy-phenyl)-[1,2,4]triazol-4-ylimino]-1,3-dihydro-indol-2-one 
• 658053-83-9 1,2-bis{4-amino-5-(p-methoxyphenyl)-1,2,4-triazol-3-ylsulfanylacetamido}ethane 
• 1021490-05-0 6-(1-chloro-3,4-dihydronaphth-2-yl)-5,6-dihydro-3-(4-methoxyphenyl)-s-triazolo[3,4-b][1,3,4]thiadiazole 
• 1085387-70-7 C₂₅H₂₄N₈O₂S₂ 
• 1085384-92-4 C₂₇H₂₈N₈O₂S₂ 
• 1119751-57-3 1,8-bis[(3-p-methoxyphenyl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl]octane 
• 85106-42-9 7H-3-(4-Methoxyphenyl)-6-phenyl-s-triazolo<3,4-b><1,3,4>thiadiazine 
• 1202208-33-0 C₁₈H₁₉N₅OS 
• 1190076-99-3 3-methyl-7-(4'-methoxyphenyl)-4H-pyrazolo[4,5-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine 
• 1190077-04-3 N-phenyl-3-(4'-nitrophenyl)-7-(4-methoxyphenyl)-4H-pyrazolo[4,5-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine 

Relevant articles and documents

Efficient Synthesis of Fluorinated [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazoles

Abstract: An efficient synthesis of fluorinated [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives has been achievedby cyclocondensation of 5-substituted 4-amino-1,2,4-triazole-3-thiols withfluoro-substituted aromatic acids using phosphoryl chloride as a cyclizingagent. The synthesized compounds were characterized by spectroscopic techniques,including IR, 1H NMR, and mass spectra.

Synthesis and computational studies of highly selective inhibitors of human recombinant tissue non-specific alkaline phosphatase (h-TNAP): A therapeutic target against vascular calcification

In this study, we have discovered small druglike molecules as selective inhibitors of human tissue-nonspecific alkaline phosphatase (h-TNAP), an enzyme critical for the regulation of extracellular matrix calcification. The upregulation of h-TNAP is associated with various pathologies particularly the vascular calcification (VC). Selective inhibition of h-TNAP over h-NPP1 may serve as a useful therapeutic strategy against vascular calcification. A series of novel triazolyl pyrazole derivatives (10a-y) in which thiol bearing triazole moiety as the zinc binding functional group was introduced to a pyrazole based pharmacophore was synthesized and evaluated as potent and selective inhibitors of h-TNAP over h-NPP1. The biological screening against h-TNAP, h-IAP, h-NPP1 and h-NPP3 showed that many of the synthesized compounds are selective inhibitors of TNAP. Particularly, the compounds 10a-h, 10j, 10m-q, 10u, 10w and 10x displayed high potency and complete selectivity towards h-TNAP over h-NPP1. Compound 10q emerged as a highly potent inhibitor (IC50 = 0.16 μM or 160 nM) against h-TNAP with 127-fold increased inhibition compared to levamisole. On the other hand, compound 10e was found to be most selective inhibitor against the tested APs and NPPs (IC50 = 1.59 ± 0.36 μM). Binding sites architecture analysis, molecular-docking and molecular dynamics simulations (MDS), revealed the basis for h-TNAP and h-IAP ligand selectivity as well as selectivity towards h-TNAP over h-NPP1. These newly discovered inhibitors are believed to represent valuable lead structures to further streamline the generation of candidate compounds to target VC.

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.