5097-86-9

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-Chlorophenyl)-1H-1,2,4-triazol-5(4H)-one is used as an antifungal agent for the treatment of fungal infections. It functions by inhibiting the enzyme cytochrome P450 14α-demethylase, which is crucial for the synthesis of ergosterol, a vital component of fungal cell membranes. The disruption of this enzyme activity leads to compromised membrane integrity, resulting in the death of fungal cells and thus treating the infection.
Additionally, 4-(4-Chlorophenyl)-1H-1,2,4-triazol-5(4H)-one is studied for its potential as an anti-tumor and anti-inflammatory agent, indicating its possible applications in oncology and inflammatory disease treatments. However, further research is required to fully understand and harness its potential in these areas.

Upstream product

• 106-47-8 4-chloro-aniline 
• 6294-89-9 hydrazinecarboxylic acid methyl ester 
• 149-73-5 trimethyl orthoformate 
• 122-51-0 orthoformic acid triethyl ester 
• 69194-89-4 p-chlorophenylsemicarbazide 
• 3473-63-0 formamidine acetic acid 

Downstream Products

• 6480-56-4 4-(4-chloro-phenyl)-2-morpholin-4-ylmethyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 155431-86-0 4-(4-chlorophenyl)-2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-3(2H,4H)-1,2,4-triazolone 
• 1042139-75-2 4-(4-chlorophenyl)-1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,4-triazol-5(4H)-one 
• 1346235-14-0 C₁₁H₁₁BrClN₃O 
• 1346235-34-4 C₁₅H₂₀ClN₅O 
• 1346235-54-8 1-(3-(4-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl) piperazin-1-yl)propyl)-4-(4-chlorophenyl)-1H-1,2,4-triazol-5(4H)-one 

Relevant academic research and scientific papers

GPR139 RECEPTOR MODULATORS

Compounds are provided that modulate the GPR139 receptor, compositions containing the same, and to methods of their preparation and use for treatment of a malcondition wherein modulation of the GPR139 receptor is medically indicated or beneficial. Such compounds have the structure of Formula (I): or a pharmaceutically acceptable isomer, racemate, hydrate, solvate, isotope, or salt thereof, wherein R1, R4, R5, R9, R10, Q6, Q7, and Q12 are as defined herein.

Design, synthesis and antifungal evaluation of 1-(2-(2,4-difluorophenyl)-2- hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,4-triazol-5(4H)-one

Based on the structure of the active site of cytochrome P450 14α-demethylase (CYP51) and the conclusions of the structure-activity relationships of azole antifungals, a series of 1-(2-(2,4-difluoro-phenyl)-2- hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,4-triazol-5(4H)-one of fluconazole analogs was synthesized. All compounds were characterized by IR, HRMS, 1HNMR and 13C NMR spectroscopic analysis. Results of preliminary antifungal in vitro test using eight human pathogenic species showed that some compounds displayed comparable or even better antifungal activities than reference drug fluconazole and that compound 3i exhibited significant activity against Candida albicans being worthy of further optimization.

Design and synthesis of novel triazole antifungal derivatives by structure-based bioisosterism

The incidence of life-threatening fungal infections is increasing dramatically. In an attempt to develop novel antifungal agents, our previously synthesized phenoxyalkylpiperazine triazole derivatives were used as lead structures for further optimization. By means of structure-based bioisosterism, triazolone was used as a new bioisostere of oxygen atom. This type of bioisosteric replacement can improve the water solubility without loss of hydrogen-bonding interaction with the target enzyme. A series of triazolone-containing triazoles were rationally designed and synthesized. As compared with fluconazole, several compounds showed higher antifungal activity with broader spectrum, suggesting their potential for further evaluations.

Process for preparation of 4-aryl-1,2,4-triazol-3-ones

A process for preparing 4-aryl-1,2,4-triazol-3-ones and 4-aryl-5-alkoxy-1,2,4-triazol-3-ones. A reaction mixture includes a primary aromatic amine, an alkyl carbazate and a trialkyl orthoformate. The reactants are heated in a reaction vessel in the presen