Chalcone derivative and application thereof

A technology for chalcone derivatives and medicines, applied in the field of chemical medicine, can solve the problem of low anti-radical activity, and achieve the effect of strong ability to scavenge free radicals and broad application prospects.

Inactive Publication Date: 2014-08-27
SHANTOU UNIV MEDICAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The present invention provides a chalcone derivative with good anti-free radical activity in order to overcome the defect of low anti-free radical activity of existing neurodegenerative drugs

Method used

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  • Chalcone derivative and application thereof
  • Chalcone derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Preparation of (E)-4-[3-hydroxyl-3-(4-bromophenyl)]propenyl-2,6-dimethoxyphenol (10b)

[0027]

[0028] 10b

[0029] Add 1.82g of syringaldehyde, 1.99g of 4-bromoacetophenone and 1mL of piperidine into a 50 mL pear-shaped bottle, quickly place it in an oil bath at 160°C, and reflux for 1 hour while stirring to obtain a dark red viscous liquid. The progress of the reaction was followed by TLC. After cooling to room temperature, under ice bath and strong stirring, add very concentrated NaOH solution to adjust the pH to above 12. Add concentrated HCl to acidify to pH 1-2. Then add a large amount of distilled water and stir vigorously to obtain a yellow turbid liquid and an orange-red oily substance. Stirring was continued, the orange-red color gradually changed to yellow, and after standing still, a large amount of yellow solids were formed. Then keep it at low temperature for a long time until the orange-red color turns yellow, filter, add an appropriate...

Embodiment 2

[0031] Example 2 Preparation of (E)-4-[3-hydroxyl-3-(4-methylphenyl)]propenyl-2,6-dimethoxyphenol (11b)

[0032]

[0033] 11b

[0034] Add 1.82g of syringaldehyde, 1.34g of 4-methylacetophenone and 1mL of piperidine into a 50 mL pear-shaped bottle, quickly place it in an oil bath at 160 °C, and reflux for 1 hour while stirring to obtain a dark red viscous liquid. Add 2-3 mL of absolute ethanol and distilled water respectively, and continue the reaction for 20 min. The progress of the reaction was followed by TLC. After the reaction is cooled to room temperature, pour it into a beaker, add another 10-15mL of distilled water, stir well, add an appropriate amount of concentrated hydrochloric acid to the reaction solution under an ice bath, stir while adding, adjust the pH to 1-2, and add a large amount of distilled water , to obtain yellow turbid liquid and orange-red oil, continue to stir, orange-red gradually turns yellow, continue to stir in the ice bath, a large amount ...

Embodiment 3

[0036] Example 3 Preparation of (E)-4-[3-hydroxyl-3-(4-methoxyphenyl)]propenyl-2,6-dimethoxyphenol (13b)

[0037]

[0038] 13b

[0039]Add 1.82g of syringaldehyde, 1.50g of 4-methoxyacetophenone and 1mL of piperidine into a 50 mL pear-shaped bottle, quickly place it in an oil bath at 160 °C, and reflux for 1 hour while stirring to obtain a dark red viscous liquid. Add 2-3 mL of absolute ethanol and continue the reaction for 20 min. The progress of the reaction was followed by TLC. After the reaction, cool to room temperature, pour the reaction solution into a large amount of cold dilute hydrochloric acid solution under the conditions of ice bath and strong stirring, and then add a large amount of distilled water to obtain a yellow turbid liquid and an orange-red oil. Continue to stir, the orange-red color gradually turns yellow. Stirring was continued in the ice bath, and a large amount of khaki solid was formed. Stir until all the orange-red turns to khaki, and filter...

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Abstract

The invention discloses a chalcone derivative with good anti-free radical oxidative damage activity. The structural formula of the chalcone derivative is shown as the following. The preparation method of the chalcone derivative includes: letting syringaldehyde and para-substituted acetophenone react in piperidine and under a high temperature so as to generate corresponding substituted chalcone; reacting purified chalcone with sodium borohydride under a cerous chloride heptahydrate condition to generate a chalcone derivative crude product, and then conducting purification. , Compared with ascorbic acid, the product provided by the invention has low anti-DPPH free radical and anti-ABTS<+> free radical IC50 value, and strong free radical scavenging ability, thus having broad application prospects in preparing drugs for treating neurodegenerative diseases. (formula I).

Description

technical field [0001] The invention belongs to the field of chemical medicine, and more specifically relates to a chalcone derivative with anti-free radical activity and a preparation method thereof. Background technique [0002] The latest census shows that there are 130 million people over the age of 60 in our country, and our country has entered an aging society ahead of schedule. Neurodegenerative diseases, such as Alzheimer's disease, Parkinson's disease and stroke, seriously endanger the health and quality of life of the elderly. [0003] At present, the pathogenesis of these diseases is not fully understood, and there is no effective treatment. However, some studies in recent years have shown that reactive oxygen species and NO free radicals produced by oxidative stress play an important role in inducing cell apoptosis and causing neurodegenerative diseases. Brain tissue is the tissue with the highest oxygen consumption and the most vigorous metabolism. It is highl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/23C07C41/26A61K31/09A61P25/28A61P25/08A61P25/16A61P39/06
CPCC07C41/26C07C43/23C07C45/74C07C49/84
Inventor 盘鹰杨芯琦郑锦鸿
Owner SHANTOU UNIV MEDICAL COLLEGE
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