[3,5-disubstituted phenyl-1-(1,2,4-triazole)]benzenesulfonic acid derivative, preparation method and applications thereof

A technology based on triazolyl and hydrazinobenzenesulfonic acid, which is applied in drug combinations, muscular system diseases, neuromuscular system diseases, etc., and can solve problems such as no treatment strategies

Pending Publication Date: 2019-10-22
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Stroke, brain injury, Alzheimer's disease, Parkinson's disease and other neurodegenerative diseases seriously affect the living standards of patients, and there is currently no effective treatment strategy

Method used

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  • [3,5-disubstituted phenyl-1-(1,2,4-triazole)]benzenesulfonic acid derivative, preparation method and applications thereof
  • [3,5-disubstituted phenyl-1-(1,2,4-triazole)]benzenesulfonic acid derivative, preparation method and applications thereof
  • [3,5-disubstituted phenyl-1-(1,2,4-triazole)]benzenesulfonic acid derivative, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1. Preparation of 4-[3-(2-hydroxyphenyl)-5-phenyl-1-(1,2,4-triazolyl)]benzenesulfonic acid amide:

[0040] Add 2g of benzoic acid and anhydrous pyridine to 20mL of xylene, add 0.7ml of thionyl chloride dropwise under stirring at room temperature, and react at room temperature for 2 hours. After the reaction is confirmed by thin-layer chromatography, distill off the solvent and residual sulfite in the reaction Acyl chloride, 30ml of xylene was added again, 2.2g of 2-hydroxybenzamide was added, the mixture was stirred under reflux at 140°C for 5-6h, and the reaction was terminated after the completion of the reaction was confirmed by thin-layer chromatography. The reaction solution was cooled to room temperature, the precipitate was filtered out, and recrystallized from ethanol to obtain a solid intermediate.

[0041] Dissolve 2 g of the intermediate in 40 ml of ethanol, add equimolar 4-hydrazinobenzenesulfonamide hydrochloride and triethylamine, heat the mixture ...

Embodiment 2

[0042] Example 2. Preparation of 4-[3-(2-hydroxyphenyl)-5-(2-hydroxyphenyl)-1-(1,2,4-triazolyl)]benzenesulfonic acid amide:

[0043] Add 2g of salicyloyl chloride to 20ml of xylene, add 1.7g of 2-hydroxybenzamide, and stir the mixture under reflux at 140°C for 5-6h, and end the reaction after confirming the completion of the reaction by thin-layer chromatography. The reaction solution was cooled to room temperature, the precipitate was filtered out, and recrystallized with ethanol to obtain a solid intermediate.

[0044] Take 2g of the intermediate and dissolve it in 40ml of ethanol, add equimolar 4-hydrazinobenzenesulfonamide hydrochloride and triethylamine, heat the mixture under reflux and stir for 16-18 hours, and end the reaction after the thin layer chromatography confirms that the reaction is complete. The reaction solution was cooled to room temperature, the precipitate was filtered, washed with water to neutrality, and recrystallized with ethanol to obtain the target ...

Embodiment 3

[0045] Example 3. 4-[3-(2-Hydroxy-4-methoxyphenyl)-5-(2-hydroxyphenyl)-1-(1,2,4-triazolyl)]benzenesulfonate Preparation of acid amides:

[0046] Add 2g of 2-hydroxy-4-methoxybenzoyl chloride to 30ml of xylene, add 1.5g of 2-hydroxybenzamide, and stir at 140°C under reflux for 5-6h. Thin-layer chromatography confirms that the reaction is complete and then ends the reaction. The reaction solution was cooled to room temperature, the precipitate was filtered out, and recrystallized from ethanol to obtain a solid intermediate.

[0047] Dissolve 2 g of the intermediate in 40 ml of ethanol, add equimolar 4-hydrazinobenzenesulfonamide hydrochloride and triethylamine, heat the mixture under reflux for 16-18 hours, and end the reaction after confirmation by thin-layer chromatography. The reaction solution was cooled to room temperature, the precipitate was filtered, washed with water to neutrality, and recrystallized with ethanol to obtain the target compound (R 1 =OH,R 2 =OCH 3 , R...

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Abstract

The invention discloses a [3,5-disubstituted phenyl-1-(1,2,4-triazole)]benzenesulfonic acid derivative, a preparation method and applications thereof, wherein a benzoic acid raw material is substituted, an acylation reaction and a condensation cyclization reaction with substituted benzamide are performed, and a reaction is performed with a p-hydrazinobenzenesulfonic acid derivative to obtain a target product [3,5-disubstituted phenyl-1-(1,2,4-triazole)]benzenesulfonic acid derivative. According to the present invention, the compound can effectively antagonize nerve cell oxidative stress damagecaused by hydrogen peroxide, sodium nitroprusside, iron ions and copper ions, can repair mitochondrial function by scavenging free radicals and restoring mitochondrial membrane potential, and has significant protection effect on neuronal cells; and the compound has neuroprotective effects of free radical scavenging and targeting mitochondria protection, and can be used for preparing drugs for prevention and treatment of neurodegenerative diseases such as stroke, brain injury, spinal cord injury, Parkinson's disease, Alzheimer's disease, amyotrophic lateral sclerosis, and the like.

Description

technical field [0001] The present invention relates to a [3,5-disubstituted phenyl-1-(1,2,4-triazolyl)]benzenesulfonic acid derivative and a preparation method thereof, and the present invention also relates to [3,5- Application of disubstituted phenyl-1-(1,2,4-triazolyl)]benzenesulfonic acid derivatives in preparation of medicines for treating or preventing neuron damage. Background technique [0002] Stroke, brain injury, Alzheimer's disease, Parkinson's disease and other neurodegenerative diseases seriously affect the living standards of patients, and currently there is no effective treatment strategy. Mitochondria are important energy-providing organelles in the brain. 90% of the oxygen molecules in the brain are consumed in the mitochondria. Oxygen, as the terminal electron acceptor of the respiratory chain, participates in the oxidative phosphorylation process of ATP production. When the nervous system is damaged and stimulated by the outside world, oxygen can produc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08A61P25/16A61P25/28A61P21/00A61P25/00
CPCC07D249/08A61P25/16A61P25/28A61P21/00A61P25/00
Inventor 张静夏廖丽萍
Owner SUN YAT SEN UNIV
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