3357-42-4

Usage

Uses

Used in Pharmaceutical Industry:
3-phenyl-2H-1,2,4-triazole is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of anti-fungal and anti-cancer drugs. Its unique structure allows for the creation of compounds with potent biological activities against various diseases.
Used in Agrochemical Industry:
In the agrochemical sector, 3-phenyl-2H-1,2,4-triazole is employed as an intermediate in the production of herbicides and fungicides. Its incorporation aids in the development of effective crop protection agents that help control pests and diseases, thereby ensuring higher crop yields and quality.
Used in Organic Synthesis:
3-phenyl-2H-1,2,4-triazole is utilized as a versatile building block in organic synthesis, enabling chemists to produce a wide array of derivatives with different functional groups and properties. This flexibility makes it a valuable component in the creation of novel compounds for various applications across multiple industries.

InChI:InChI=1/C8H7N3/c1-2-4-7(5-3-1)8-9-6-10-11-8/h1-6H,(H,9,10,11)

Upstream product

• 3414-94-6 5-phenyl-1,2-dihydro-1,2,4-triazole-3-thione 
• 38345-23-2 4-amino-3-phenyl-1,2,4-triazole 
• 1627-73-2 1-benzylidene thiosemicarbazide 
• 613-94-5 benzoic acid hydrazide 
• 77287-34-4 formamide 
• 825-60-5 benzimidic acid ethyl ester 
• 624-84-0 formic acid hydrazide 
• 2227-79-4 benzenecarbothioamide 
• 15795-40-1 1-acetyl-3-phenyl-1,2,4-triazole 
• 55-21-0 benzamide 
• 18162-28-2 5-phenyl-1,2,4-triazine 
• 825-56-9 2-phenyl-1,3,4-oxadiazole 
• 79746-00-2 1-benzoyl-3-phenyl-1,2,4-triazole 
• 22839-47-0 L-Asp-L-Phe-OMe 

Downstream Products

• 39696-58-7 1-methyl-3-phenyl-1H-1,2,4-triazole 
• 29945-53-7 1-methyl-5-phenyl-1H-1,2,4-triazole 
• 23159-64-0 3-phenyl-1-propionyl-1H-[1,2,4]triazole 
• 15795-40-1 1-acetyl-3-phenyl-1,2,4-triazole 
• 38345-37-8 1-benzyl-3-phenyl-1,2,4-1H-triazole 
• 1092852-58-8 1-(3-phenyl-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone 
• 1187181-59-4 C₁₃H₁₃N₃O 
• 114505-93-0 C₁₇H₁₁N₃O₂ 
• 1185190-44-6 4-(3,5-dimethylphenylsulfanyl)-3-iodo-6-methyl-5-(3-phenyl-[1,2,4]triazol-1-ylmethyl)pyridin-2(1H)-one 
• 1185190-97-9 4-(3,5-dimethylphenylsulfanyl)-3-iodo-6-methyl-5-(3-phenyl-[1,2,4]triazol-4-ylmethyl)pyridin-2(1H)-one 
• 25433-29-8 2-(3-phenyl-1H-1,2,4-triazol-5-yl)-pyridine 
• 23164-60-5 4-(3-phenyl-1H-1,2,4-triazol-5-yl)pyridine 
• 89804-59-1 3-phenyl-5-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole 

Relevant academic research and scientific papers

Quantitative analysis of solvent effects in highly aqueous media. Application of the SWAG procedures and a critical appraisal of the additivity principle

This paper describes a study on medium effects of 25 monohydric and polyhydric alcohols on the neutral hydrolysis of 1-benzoyl-3-phenyl-1,2,4-triazole in highly aqueous media. Dependences of pseudo-first-order rate constants on molality of added alcohol are quantitatively analyzed in terms of pairwise Gibbs energy interaction parameters for initial state and transition state. Additivity of pairwise group interaction parameters (SWAG procedure) is applied, and the validity of additivity is critically examined. Excellent additivity is observed in series of monohydric alcohols and vicinal diols. In series of polyhydric alcohols, group contributions to the observed rate effects, as expressed in pairwise group interaction parameters, are, however, strongly dependent on the position of hydroxyl groups in the alcohol. This (apparent) nonadditivity behavior is discussed in terms of the hydration characteristics of the cosolvents. The importance of hydration shell overlap in determining medium effects is supported by kinetic data in ternary 1-propanol-urea-water mixtures.

General-base catalysed hydrolysis and nucleophilic substitution of activated amides in aqueous solutions

The reactivity of 1-benzoyl-3-phenyl-1,2,4-triazole (1a) was studied in the presence of a range of weak bases in aqueous solution. A change in mechanism is observed from general-base catalysed hydrolysis to nucleophilic substitution and general-base catalysed nucleophilic substitution. A slight tendency is also observed for the more hydrophobic general bases to show higher reactivity towards 1a. Aspartame is an effective nucleophile, possibly because nucleophilic substitution is subject to intramolecular general-base catalysis. A general conclusion derived from the present results is that unexpected rate effects can only be rationalised provided that the detailed reaction mechanisms are well understood. Copyright

Synthesis of novel 1,2,4-trizaole- and isoxazol(in)e-containing heterocycles

A route for the regiospecific synthesis of 3-(triazol-3-yl)-1,2-isoxazol(in)e-5-yl-aryl derivatives has been developed by intermolecular 1,3-dipolar cycloaddition chemistry, and novel annulated compounds having triazole/isoxazole have been prepared by emp

Perturbation of SDS and CTAB Micelles by Complexation with Poly(ethylene oxide) and Poly(propylene oxide)

Pseudo-first-order rate constants have been determined for the neutral hydrolysis of 1-benzoyl-3-phenyl-1,2,4-triazole in aqueous solutions in the presence of SDS and CTAB micelles and SDS-PEO, SDS-PPO, and CTAB-PPO mixed micelles.The micellar rate inhibition of the hydrolysis is clearly modified as a result of micelle-polymer complexation, the effects being rather specific for the nature of the surfactant and the polymer.The kinetic data were analyzed by a simple pseudophase model.The results revealed stabilization of the micelles by interaction with the polymer and polymer-induced microenvironmental changes at the micellar binding sites of the substrate.Results from conductivity measurements facilitated the interpretation of the kinetic data.

Association of Hydrotropes in Aqueous Solution Studied by Reaction Kinetics

The effect of added hydrotropes on the rates of neutral hydrolysis for 1-benzoyl-3-phenyl-1,2,4-triazole 1 has been studied, together with the concentration dependence of the 1H NMR spectra of the hydrotropes in aqueous solution. Hydrotropes include sodium 4-alkylbenzenesulfonates 2a-e, sodium 4-methoxybenzenesulfonate 2f, sodium 4-hydroxybenzenesulfonate 2g, cesium benzenesulfonate 3, benzamidinium chloride 4, phenyltrimethylammonium bromide 5a, and benzyltrimethylammonium bromide 5b. All hydrotropes, except 2g, induce strong rate-retarding effects, indicative of strong interactions with 1 and of remarkably strong hydrophobic interactions between aromatic moieties. Most hydrotropes show neither spectroscopic nor kinetic evidence for cooperative aggregation in the concentration range studied, i.e., from 0 to 1.4 mol kg-1. Cooperative aggregation is absent because the Hydrophobic moieties are too small for hydrophobic interactions to overcome electrostatic repulsion. Lack of aggregation results in high availability of hydrophobic binding sites, thereby accounting for the high solubilizing power characteristic for hydrotropes. However, sodium 4-n-propylbenzenesulfonate 2d and sodium 4-n-butylbenzenesulfonate 2e show cooperative self-association forming highly dynamic loose micellar-type structures.

Stereochemical Aspects of Hydration of Carbohydrates in Aqueous Solutions. 2. Kinetic Medium Effects

Rate constants for the hydrolysis of 1-benzoyl-3-phenyl-1,2,4-triazole in aqueous solutions of carbohydrates have been measured as a function of molality and nature of added mono- and disaccharides.The kinetic medium effects induced by the carbohydrates originate from hydration sphere overlap effects.The results are analyzed using the additivity principle and reveal specificity in the stereochemical aspects of hydration.The major effect determining the hydration of a monosaccharide appears to be the position of the OH(4) group in conjunction with OH(2).The positionof the carbonyl function and the number of equatorial groups present in the molecule are of minor importance.The experimentally obtained G(C) values, which are representative of the interaction between the carbohydrate and the initial state and activated complex for the hydrolysis reaction, show that the hydration of the carbohydrates is mainly determined by the methine moieties.The G(CHOH, endo) values obtained for the dominant conformers in solution point to similar conclusion.With an increase in compatibility of the carbohydrate molecule with the three-dimensional hydrogen-bond structure of water, the hydroxy groups become less important in determining carbohydrate-solute interactions.This might be important in molecular recognition, since under these conditions the carbohydrates are recognized as hydrophobic moieties.For disaccharides the medium effects are larger than expected on the basis of the medium effect of two monosaccharide subunits.We suggest that this is caused by a cooperativity effect, which makes the methine moieties even more dominant in governing the hydration characteristics.The G(C) values reveal that thetype of linkage in the disaccharide molecule hardly influences the kinetic medium effect.Only when one of the monosaccharide subunits has an axial OH(4) or when there is a 1-3 type of linkage between the moieties is a significantly different G(C) found.It is suggested that the compatibility of the carbohydrates with the three-dimensional hydrogen-bond structure of water largely depends on the compatibility of the next nearest neighbor oxygens of the carbohydrate molecule with the nearest or next nearest neighbor oxygens of liquid water.

Liganding Functional Tyrosine Sites on Proteins Using Sulfur-Triazole Exchange Chemistry

Tuning reactivity of sulfur electrophiles is key for advancing click chemistry and chemical probe discovery. To date, activation of the sulfur electrophile for protein modification has been ascribed principally to stabilization of a fluoride leaving group (LG) in covalent reactions of sulfonyl fluorides and arylfluorosulfates. We recently introduced sulfur-triazole exchange (SuTEx) chemistry to demonstrate the triazole as an effective LG for activating nucleophilic substitution reactions on tyrosine sites of proteins. Here, we probed tunability of SuTEx for fragment-based ligand discovery by modifying the adduct group (AG) and LG with functional groups of differing electron-donating and -withdrawing properties. We discovered the sulfur electrophile is highly sensitive to the position of modification (AG versus LG), which enabled both coarse and fine adjustments in solution and proteome activity. We applied these reactivity principles to identify a large fraction of tyrosine sites (～30%) on proteins (～44%) that can be liganded across >1500 probe-modified sites quantified by chemical proteomics. Our proteomic studies identified noncatalytic tyrosine and phosphotyrosine sites that can be liganded by SuTEx fragments with site specificity in lysates and live cells to disrupt protein function. Collectively, we describe SuTEx as a versatile covalent chemistry with broad applications for chemical proteomics and protein ligand discovery.

Design, synthesis, and biological activity of novel tetrahydropyrazolopyridone derivatives as FXa inhibitors with potent anticoagulant activity

A series of novel tetrahydropyrazolopyridone derivatives containing 1,3,4-triazole, triazolylmethyl, and partially saturated heterocyclic moieties as P2 binding element was designed, synthesized, and evaluated in vitro for anticoagulant activity in human and rabbit plasma. All compounds showed moderate to significant potency, and compounds 15b, 15c, 20b, 20c, and 22b were further examined for their inhibitory activity against human FXa in vitro. While compounds 15c and 22b were tested for rat venous thrombosis in vivo. The most promising compound 15c, with an IC50 (FXa) value of 0.14?μM and 98% inhibition rate, warranted further investigation as an FXa inhibitor.

A new, high-yield synthesis of 3-aryl-1,2,4-triazoles

A convenient new synthetic approach to 3-aryl-1,2,4-triazoles has been developed. Chloralamides were obtained by high yield reactions between benzamides and chloral hydrate. These reacted with a phosphorus pentachloride/phosphorus oxychloride mixture unde

PDE10 MODULATORS

The present invention relates to compounds of formula (I) wherein R1, R2, R3, R5, W, X, X1, Y, Y1, Z and Z1 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit PDE10A and can be used in the treatment of CNS disorders such as schizophrenia, Alzheimer's disease, and Parkinson's disease.