149622-77-5

Basic information

• Product Name: 5-(4-AMINO-PHENYL)-4-METHYL-4 H-[1,2,4]TRIAZOLE-3-THIOL
• Synonyms: 5-(4-AMINO-PHENYL)-4-METHYL-4 H-[1,2,4]TRIAZOLE-3-THIOL;3-(4-aminophenyl)-4-methyl-1H-1,2,4-triazole-5-thione
• CAS NO: 149622-77-5
• Molecular Formula: C₉H₁₀N₄S
• Molecular Weight: 206.27
• Mol File: 149622-77-5.mol

Chemical Properties

• Melting Point: 178 °C
• Boiling Point: 337°C at 760 mmHg
• Flash Point: 157.6°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 0.000108mmHg at 25°C
• Refractive Index: 1.731
• PKA: 8.81±0.20(Predicted)
• CAS DataBase Reference: 5-(4-AMINO-PHENYL)-4-METHYL-4 H-[1,2,4]TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-AMINO-PHENYL)-4-METHYL-4 H-[1,2,4]TRIAZOLE-3-THIOL(149622-77-5)
• EPA Substance Registry System: 5-(4-AMINO-PHENYL)-4-METHYL-4 H-[1,2,4]TRIAZOLE-3-THIOL(149622-77-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 149622-77-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-(4-Amino-phenyl)-4-methyl-4H-[1,2,4]triazole-3-thiol is used as an active pharmaceutical ingredient for the development of antifungal and antibacterial drugs. Its sulfur-containing ring structure provides it with unique properties that can be exploited to target and eliminate harmful microorganisms.
Used in Medicinal Chemistry Research:
5-(4-Amino-phenyl)-4-methyl-4H-[1,2,4]triazole-3-thiol is used as a building block in the synthesis of more complex molecules with potential therapeutic uses. Its unique structure allows for the development of new drugs with improved efficacy and reduced side effects.
Used in Drug Synthesis:
5-(4-Amino-phenyl)-4-methyl-4H-[1,2,4]triazole-3-thiol is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its versatile chemical properties enable it to be incorporated into a wide range of drug molecules, enhancing their therapeutic potential.
Used in Antimicrobial Agents:
5-(4-Amino-phenyl)-4-methyl-4H-[1,2,4]triazole-3-thiol is used as an antimicrobial agent in various applications, such as in the development of new antibiotics, antifungal creams, and disinfectants. Its ability to target and eliminate harmful microorganisms makes it a valuable component in the fight against drug-resistant infections.
Used in Chemical Synthesis:
5-(4-Amino-phenyl)-4-methyl-4H-[1,2,4]triazole-3-thiol is used as a reagent in various chemical synthesis processes. Its unique structure and properties make it a valuable component in the production of a wide range of chemical compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C9H10N4S/c1-13-8(11-12-9(13)14)6-2-4-7(10)5-3-6/h2-5H,10H2,1H3,(H,12,14)

Upstream product

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• 146305-30-8 1--4-methylthiosemicarbazide 

Downstream Products

• 360559-33-7 4-[5-(2,4-dichloro-benzylsulfanyl)-4-methyl-4H-[1,2,4]triazol-3-yl]-phenylamine 
• 1055325-98-8 5-[4-(4,6-dimorpholin-4-yl-[1,3,5]triazin-2-ylamino)phenyl]-4-methyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 498537-27-2 2-(5-(4-aminophenyl)-4-methyl-4H-1,2,4-triazol-3-ylthio)-N-(2-(2-(benzylamino)-2-oxoethylthio)benzo[d]thiazol-6-yl)acetamide 

Relevant articles and documents

Synthesis, antifungal activity, 3d-qsar, and molecular docking study of novel menthol-derived 1,2,4-triazole-thioether compounds

A series of novel menthol derivatives containing 1,2,4-triazole-thioether moiety were designed, synthesized, characterized structurally, and evaluated biologically to explore more potent natural product-based antifungal agents. The bioassay results reveal

A High-Throughput Glycosyltransferase Inhibition Assay for Identifying Molecules Targeting Fucosylation in Cancer Cell-Surface Modification

In cancers, increased fucosylation (attachment of fucose sugar residues) on cell-surface glycans, resulting from the abnormal upregulation of the expression of specific fucosyltransferase enzymes (FUTs), is one of the most important types of glycan modifications associated with malignancy. Fucosylated glycans on cell surfaces are involved in a multitude of cellular interactions and signal regulation in normal biological processes, as well as in disease. For example, sialyl LewisX is a fucosylated cell-surface glycan that is abnormally abundant in some cancers where it has been implicated in facilitating metastasis, allowing circulating tumor cells to bind to the epithelial tissue within blood vessels and invade into secondary sites by taking advantage of glycan-mediated interactions. To identify inhibitors of FUT enzymes as potential cancer therapeutics, we have developed a novel high-throughput assay that makes use of a fluorogenically labeled oligosaccharide as a probe of fucosylation. This probe, which consists of a 4-methylumbelliferyl glycoside, is recognized and hydrolyzed by specific glycoside hydrolase enzymes to release fluorescent 4-methylumbelliferone, yet when the probe is fucosylated prior to treatment with the glycoside hydrolases, hydrolysis does not occur and no fluorescent signal is produced. We have demonstrated that this assay can be used to measure the inhibition of FUT enzymes by small molecules, because blocking fucosylation will allow glycosidase-catalyzed hydrolysis of the labeled oligosaccharide to produce a fluorescent signal. Employing this assay, we have screened a focused library of small molecules for inhibitors of a human FUT enzyme involved in the synthesis of sialyl LewisX and demonstrated that our approach can be used to identify potent FUT inhibitors from compound libraries in microtiter plate format.

Design, synthesis and antibacterial evaluation of 1-[(1R,2S)-2-Fluorocyclopropyl] Ciprofloxacin-(4-Methyl-3-Aryl)-1,2,4-Triazole-5(4H)-Thione Hybrids

Fourteen novel 1-[(1R,2S)-2-Fluorocyclopropyl]ciprofloxac in-(4-methyl-3-aryl)-1,2,4-triazole-5(4H)-thione hybrids 6a-n were designed, synthesized and assessed for their in vitro antibacterial activities against representative Gram-positive and Gram-negat

Synthesis and invitro Evaluation of West Nile Virus Protease Inhibitors Based on the 2-{6-[2-(5-Phenyl-4H-{1,2,4]triazol-3-ylsulfanyl)acetylamino]benzothiazol-2-ylsulfanyl}acetamide Scaffold

In recent years, clinical symptoms resulting from West Nile virus (WNV) infection have worsened in severity, with an increased frequency in neuroinvasive diseases among the elderly. As there are presently no successful therapies against WNV for use in humans, continual efforts to develop new chemotherapeutics against this virus are highly desired. The viral NS2B-NS3 protease is a promising target for viral inhibition due to its importance in viral replication and its unique substrate preference. In this study, a WNV NS2B-NS3 protease inhibitor with a 2-{6-[2-(5-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl)acetylamino]benzothiazol-2-ylsulfanyl}acetamide scaffold was identified during screening. Optimization of this initial hit by synthesis and screening of a focused compound library with this scaffold led to the identification of a novel uncompetitive inhibitor (1a24, IC50=3.4±0.2μM) of the WNV NS2B-NS3 protease. Molecular docking of 1a24 into the WNV protease showed that the compound interferes with productive interactions of the NS2B cofactor with the NS3 protease and is an allosteric inhibitor of the WNV NS3 protease.

Selective modification of bifunctional heterocyclic compounds containing amino and thioamide groups in acetic acid medium

(Chemical Equation Presented) In acetic acid medium, 2-chloro-4,6- dimorpholin-4-yl-[1,3,5]triazine undergoes amination by bifunctional heterocyclic compounds containing both amino and thioamide groups. The reactions are high-yielding and selective; the t

Synthesis and primary cytotoxicity evaluation of new diaryltriazenes

A series of triazenes derived from 5-(4-aminophenyl)-2,4-dihydro-4- substituted-3H-1,2,4-triazole-3-thiones 1a-c, aminoglutethimide or para-aminobenzoic acid have been synthesized for in vitro anticancer properties against three cell lines. The selected c

Synthesis of some 3-(Arylalkylthio)-4-alkyl/aryl-5-(4-aminophenyl)-4H-1,2, 4-triazole derivatives and their anticonvulsant activity

A series of novel 3-{[(substituted phenyl)methyl]thio}-4-alkyl/aryl-5-(4- aminophenyl)-4H-1,2,4-triazoles 11-20 and several related Schiff's bases, 3-{[(substituted phenyl)-methyl]thio}-4-alkyl/aryl-5-{[[(substituted phenyl/5-nitro-2-furyl)methylene]amino

Synthesis, characterization of novel coupling products and 4-arylhydrazono-2-pyrazoline-5-ones as potential antimycobacterial agents

Novel coupling products 7a-d and 4-arylhydrazono-2-pyrazoline-5-ones 8a-e were synthesized and evaluated for antimycobacterial activity against Mycobacterium tuberculosis H37Rv and Mycobacterium avium. Compound 7b was found to be the most potent derivatives of the 7a-d series by an MIC value of 6.25 μg/ml.

Some 3-Thioxo/Alkylthio-1,2,4-triazoles with a Substituted Thiourea Moiety as Possible Antimycobacterials

A series of novel N-alkyl/aryl-N'-[4-(4-alkyl/aryl-2,4-dihydro-3H-1,2,4-triazole-3-thione-5-yl)phenyl]thioureas 1-19 and three S-alkylated representatives of the former, N-alkyl/aryl-N'-[4-(3-aralkylthio-4-alkyl/aryl-4H-1,2,4-triazole-5-yl)phenyl]thioureas 20-22, were synthesized and tested for antimycobacterial activity against Mycobacterium tuberculosis H37Rv as well as Mycobacterium fortuitum ATCC 6841 which is a rapid growing opportunistic pathogen. Compounds 4 and 9-11 were found to possess the same MIC value with that of Tobramycin against M. fortuitum ATCC 6841 whereas 1-3 and 21 had positive response against M. tuberculosis H37Rv at varying degrees. Compound 21 was identified as the most potent derivative of the 1-22 series by an MIC value of 6.25 μg/ml and selectivity index of 1.6