6232-82-2

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Triazole-3-thione,2,4-dihydro-5-methyl-4-phenyl-3H-1 is used as a key intermediate in the synthesis of various pharmaceuticals. Its biological activity and potential as an antiviral, anti-inflammatory, and anticancer agent make it a valuable compound for the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical industry, 2,4-Triazole-3-thione,2,4-dihydro-5-methyl-4-phenyl-3H-1 is utilized in the synthesis of agrochemicals, such as pesticides and herbicides. Its potential applications in this field contribute to the development of more effective and environmentally friendly products.
Used in Materials Science:
2,4-Triazole-3-thione,2,4-dihydro-5-methyl-4-phenyl-3H-1 also has potential applications in materials science, where it can be used to develop new materials with unique properties. Its versatility and ability to form metal complexes make it a promising candidate for use in coordination chemistry and metal complexation.
Used as a Ligand in Coordination Chemistry:
2,4-Triazole-3-thione,2,4-dihydro-5-methyl-4-phenyl-3H-1 is used as a ligand in coordination chemistry, where it can form metal complexes with various applications, such as catalysts, sensors, and materials with specific properties.

InChI:InChI=1/C9H15N3S/c1-7-10-11-9(13)12(7)8-5-3-2-4-6-8/h8H,2-6H2,1H3,(H,11,13)

Upstream product

• 13153-00-9 N⁴-phenyl acetic acid thio-semicarbazide 
• 141-78-6 ethyl acetate 
• 5351-69-9 4-Phenyl-3-thiosemicarbazide 
• 78-39-7 Triethyl orthoacetate 
• 25835-31-8 C₅H₁₁N₃OS 
• 62-53-3 aniline 
• 103-72-0 phenyl isothiocyanate 
• 1068-57-1 acetic acid hydrazide 
• 18871-66-4 N,N-dimethylacetamide dimethyl acetal 
• 53278-51-6 S-(phenylthiocarbamoyl)thioglycolic acid 

Downstream Products

• 105909-29-3 3-ethylthio-5-methyl-4-phenyl-4H-1,2,4-triazole 
• 40279-27-4 3-Methyl-5-methylthio-4-phenyl-4H-1,2,4-triazole 
• 109260-70-0 3-ethyl-5-[(5-ethylmercapto-2-methyl-4-phenyl-2,4-dihydro-[1,2,4]triazol-3-yliden)-ethylidene]-2-thioxo-thiazolidin-4-one 
• 1355947-29-3 1,2,4,5-tetrakis(5-methyl-4-phenyl-1,2,4-triazol-3-ylthiomethyl)benzene 
• 62372-96-7 2-[(5-methyl-4-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]-N-[(2-hydroxyphenyl)methylidene]acetohydrazide 
• 62373-03-9 2-[(5-methyl-4-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]-N-[(3-nitrophenyl)methylidene]acetohydrazide 
• 62373-01-7 2-[(5-methyl-4-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]-N-[(4-methoxyphenyl)methylidene]acetohydrazide 
• 13576-42-6 3-methyl-4-phenyl-4H-1,2,4-triazole 
• 354995-89-4 N-(2-chloro-phenyl)-2-(5-methyl-4-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl)-acetamide 
• 84210-55-9 ethyl [(4-phenyl-5-methyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetate 
• 1428354-39-5 4-cyclohexyl-1-{[(4-phenyl-5-methyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetyl} thiosemicarbazide 
• 1428354-38-4 4-(4-methoxybenzyl)-1-{[(4-phenyl-5-methyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetyl} thiosemicarbazide 
• 1428354-37-3 4-benzyl-1-{[(4-phenyl-5-methyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetyl} thiosemicarbazide 

Relevant academic research and scientific papers

Amphiphilic silicone-bridged bis-triazoles as effective, selective metal ligands and biologically active agents in lipophilic environment

Pairs of different substituted 3-mercapto-1,2,4-triazole units are coupled, through thioether bridges, to organic-inorganic substrates consisting in short hydrophobic silicone segment. A library of six compounds are isolated as crystalline solids and structurally characterized by X-ray single crystal diffraction, elemental, spectral and thermal analysis. The flexibility of the silicone spacer makes the small molecular compounds exhibit glass transition in the negative domain. The metal binding capacity is evaluated by quantum mechanics calculations, the results being in line with experimental data obtained by UV–vis spectroscopy titration. The results indicate that the prepared compounds can act as ligands for metal ions with high selectivity for Cu2+, an element of interest in biological processes, forming 1:1 stable mononuclear complexes with an association constant up to 8.87 × 103 M?1. The presence of the highly hydrophobic silicone spacer makes the behavior of bis-triazoles obtained more sensitive to the nature of the environment. The preliminary bioassay indicates lipophilic medium more suitable for biocide action of silicone-bridged bis-triazoles, which in some cases far exceeds that of reference. The mechanism of enzyme inhibition is demonstrated by molecular docking, and the results indicate that, in all docked complexes, the ligands are directly coordinated to the heme ferric iron.

COMPOUNDS FOR MODULATING AQUAPORINS

The invention relates to compounds of formula (I) pharmaceutical compositions thereof and methods for modulating aquaporin 9.

Polymeric Cd(II), trinuclear and mononuclear Ni(II) complexes of 5-methyl-4-phenyl-1,2,4-triazole-3-thione: Synthesis, structural characterization, thermal behaviour, fluorescence properties and antibacterial activity

Syntheses of a polymeric Cd(II) complex, [Cd(mptt)2]n (1), a trinuclear Ni(II) complex, [Ni3(μ-mptt)4(μ-H2O)2(H2O)2(ttfa)2]·3H2O (2) and a mononuclear Ni(II) complex [Ni(mptt)2(en)2] (3) have been performed using the ligand 5-methyl-4-phenyl-1,2,4-triazole-3-thione (Hmptt) and nickel(II)/cadmium(II) salts {ttfa = thenoyltrifluroacetonate). The ligand and the complexes have been characterized by various physicochemical methods in addition to their single crystal X-ray structure. The Cd centre in complex 1 adopts a distorted tetrahedral geometry with one sulfur atom and two mptt ligands provide three nitrogen atoms from three triazole units. The sulfur atom of the ligand binds covalently and overall the ligand acts as uninigative N,S/N,N bidentate moiety. The polymeric structure of complex 1 results from the N atoms of the neighboring triazole units coordinating with the Cd(II) centre. The three Ni(II) centres in the trinuclear Ni(II) complex 2 form a linear arrangement and all have six coordinated arrangements. The middle Ni(II) binds with four deprotonated triazole ring nitrogens and two water molecules form two bridges. The terminal Ni(II) centres bind through two thenoyl oxygens, two triazole nitrogens and water molecules that formed bridges with the middle Ni centre. In complex 3, the nickel(II) centre is covalently bonded through two deprotonated triazole ring nitrogens from two ligand moieties and other four sites are occupied by four nitrogens from two bidentate en ligands. Thermogravimetric analyses (TGA) of the complexes indicated for NiO as the final residue. The bioefficacy of the ligand and complexes 2 and 3 have been examined against the growth of bacteria to evaluate their anti-microbial potential. Complex 2 showed high antibacterial activity as compared to the ligand and complex 3. Complexes 1, 2 and 3 are fluorescent materials with maximum emissions at 425, 421 and 396 nm at an excitation wavelength of 323, 348 and 322 nm, respectively.

Preparation and antibacterial properties of substituted 1,2,4-triazoles

Background. Both 1,2,3- and 1,2,4-triazoles are nowadays incorporated in numerous antibacterial pharmaceutical formulations. Aim. Our study aimed to prepare three substituted 1,2,4-triazoles and to evaluate their antibacterial properties. Materials and Methods. One disubstituted and two trisubstituted 1,2,4-triazoles were prepared and characterised by physical and spectroscopic properties (melting point, FTIR, NMR, and GC-MS). The antibacterial properties were studied against three bacterial strains: Staphylococcus aureus (ATCC 25923), Escherichia coli (ATCC 25922), and Pseudomonas aeruginosa (ATCC 27853), by the agar disk diffusion method and the dilution method with MIC (minimal inhibitory concentration) determination. Results. The spectroscopic characterization of compounds and the working protocol for the synthesis of the triazolic derivatives are described. The compounds were obtained with 15-43% yields and with high purities, confirmed by the NMR analysis. The evaluation of biological activities showed that the compounds act as antibacterial agents against Staphylococcus aureus (ATCC 25923), while being inactive against Escherichia coli (ATCC 25922) and Pseudomonas aeruginosa (ATCC 27853). Conclusions. Our results indicate that compounds containing 1,2,4-triazolic moiety have great potential in developing a wide variety of new antibacterial formulations.

Antimicrobial and Physicochemical Characterizations of Thiosemicarbazide and S-Triazole Derivatives

Two series of thiosemicarbazide derivatives and three series of s-triazole derivatives have been synthesized. All of these compounds were tested for their in vitro antibacterial activity against Gram-positive and Gram-negative bacterial strains. Among tested thiosemicarbazide derivatives, the best bioactivity was detected for two 1-formylthiosemicarbazides with 3-/4-tolyl substitution (1 l, 1 m) (MICs range between 31.25 and 250 μg/mL). All tested s-triazole derivatives exhibited lower antibacterial activity than their acyclic precursors.

Synthesis of 1,2,4,5-tetrakis(1,2,4-triazolyl) benzene and 1,2,4,5-tetrakis(1,3,4-oxadiazolyl) benzene derivatives

A series of 1,2,4,5-tetrakis(1,2,4-triazolyl)benzenes and 1,2,4,5-tetrakis(1,3,4-oxadiazolyl)benzenes was synthesized by nucleophilic addition of sodium salts of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 1,3,4-oxadiazole-2(3H)-thiones to 1,2,4,5-tetrakis(bromomethyl)benzene. The structure of the newly synthesized compounds was confirmed by elemental analysis, IR and 1H and 13C NMR spectra. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: 1H and 13C NMR spectra of products (Figures S1-S24).

Determination of the lipophilicity of some new derivatives of thiosemicarbazide and 1,2,4-triazoline-5-thione with potential antituberculosis activity

The chromatographic behavior of newly obtained derivatives of thiosemicarbazide and 1,2,4-triazoline-5-thione was determined. The lipophilicity was confirmed by the use of the Reversed Phase Thin-Layer Chromatography (RP-TLC) method. For both groups of solutes the lipophilicity depended on the substituents. All obtained compounds were tested for their antimycotic activity. The strongest antituberculosis activity was observed for 4-(2-iodophenyl)-1-(pyridine-4-ylacetyl)thiosemicarbazide 4 and 4-phenyl-3-(pyridine-4-ylmethyl)-1,2,4-triazoline-5-thione 27.

Synthesis and biological evaluations of sulfanyltriazoles as novel HIV-1 non-nucleoside reverse transcriptase inhibitors

A novel sulfanyltriazole was discovered as an HIV-1 non-nucleoside reverse transcriptase inhibitor via HTS using a cell-based assay. Chemical modifications and molecular modeling studies were carried out to establish its SAR and understand its interactions with the enzyme. These modifications led to the identification of sulfanyltriazoles with low nanomolar potency for inhibiting HIV-1 replication and promising activities against selected NNRTI resistant mutants. These novel and potent sulfanyltriazoles could serve as advanced leads for further optimization.

A one-pot synthesis of 4,5-disubstituted-1,2,4-triazole-3-thiones on solid support under microwave irradiation

4,5-Di-substituted-1,2,4-triazole-3-thiones (4a-f) have been prepared in one stage from the reaction of acid hydrazide 1 with alkyl or aryl isothiocyanate 2 in the presence of a KOH (10%) solution on the surface of silica gel as well as on the surface of montmorillonite K10 under microwave irradiation. These triazoles have also been prepared from the reaction of 4-substituted-1-aroyl thiosemicarbazides 3a-e, with a KOH (10%) solution on the surface of silica gel under microwave irradiation. Copyright Taylor & Francis Group, LLC.