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A kind of chalcone derivative and its application

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

Inactive Publication Date: 2016-03-02
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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  • A kind of chalcone derivative and its application
  • A kind of chalcone derivative and its application
  • A kind of chalcone derivative and its application

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 50mL pear-shaped bottle, quickly place it in an oil bath at 160°C, and reflux for 1h 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 amou...

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 50mL 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 of...

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 50mL 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 oxidation damage activity, and its structural formula is as follows. The preparation method of the chalcone derivatives is as follows: syringaldehyde and p-substituted acetophenone react under conditions of piperidine and high temperature to generate corresponding substituted chalcones; the purified chalcone and sodium borohydride react in seven React under the condition of water cerium trichloride to generate crude chalcone derivatives, which can be obtained after purification. The ascorbic acid product of the invention has a low IC50 value for anti-DPPH free radicals and anti-ABTS+ free radicals, and has a strong ability to scavenge free radicals, and has broad application prospects in the preparation of drugs for treating neurodegenerative diseases.

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 Patents(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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