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7 and 20 dehydro-silybin dialky ether and preparation method and medicine use thereof

A technology of silibinin and dehydrogenated water, which is applied in the direction of drug combinations, pharmaceutical formulas, and medical preparations containing active ingredients, can solve the problems of changes and damage of the biphospholipid layer of the cell membrane, and achieve a strong anti-lipid overload. Oxidation, simplicity of the method, and the effect of protecting the metal ion chelating ability

Inactive Publication Date: 2012-12-05
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In addition, active oxygen can cause changes and damage to the biphospholipid layer of the cell membrane, and the destruction of some biphospholipid layers directly causes the cause of AD [Nitsch, R.M., Proc.Natl.Acad.SCi.U.S.A.1992, 89:1671-1675]

Method used

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  • 7 and 20 dehydro-silybin dialky ether and preparation method and medicine use thereof
  • 7 and 20 dehydro-silybin dialky ether and preparation method and medicine use thereof
  • 7 and 20 dehydro-silybin dialky ether and preparation method and medicine use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 : the preparation of compound I-a i.e. 7,20-bisallyl-dehydrosilibinin ether

[0031]

[0032] In a dry reaction flask, 0.240 g of silibinin was dissolved in 4 ml of DMF, 0.276 g of potassium carbonate was added, and stirred for 10 minutes to dissolve completely. 0.125 g of allyl bromide was slowly added dropwise, stirred for 10 minutes, and then heated at 75°C for 3 hours. Stand to cool, add 20 ml of distilled water, extract with ethyl acetate three times (10 ml each time), combine the organic layers, wash with 20 ml of distilled water, dry over anhydrous sodium sulfate, and concentrate under reduced pressure. The brown-yellow crude product was obtained, and it was eluted with 200-300 mesh silica gel (10 g) with chloroform: ethyl acetate: acetic acid = 20:1:0.1 to obtain 74.3 mg of yellow crystal (I-a). Yield 26.6%.

[0033] Compound I-a name: 2-[2,3-dihydro-3-(4-allyloxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxane -6-]-7-(allyloxy)-3,5,-dihydroxy...

Embodiment 2

[0034] Example 2 : Compound I-b is the preparation of 7,20-bis(1-butenyl)-dehydrosilibinin ether

[0035] In a dry reaction flask, 0.240 g of silibinin was dissolved in 4 ml of DMF, 0.276 g of potassium carbonate was added, and stirred for 10 minutes to dissolve completely. 0.135 g of 4-bromo-1-butene was slowly added dropwise, stirred for 10 minutes, and then heated at 75°C for 3 hours. Stand to cool, add 20 ml of distilled water, extract with ethyl acetate three times (10 ml each time), combine the organic layers, wash with 20 ml of distilled water, dry over anhydrous sodium sulfate, and concentrate under reduced pressure. The brownish-yellow crude product was subjected to column chromatography on 200-300 mesh silica gel (10 g), eluted with chloroform: ethyl acetate: acetic acid = 20:1:0.1, and 70 mg of yellow crystal (I-b) was obtained. Yield 23.8%.

[0036] Compound I-b name: 2-[2,3-dihydro-3-(4-enbutyloxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxane -6-]-7-(en...

Embodiment 3

[0037] Example 3 : Compound I-c is 7, the preparation of 20-bis(2-methyl-2-ene butyl)-dehydrosilibinin ether

[0038]

[0039] In a dry reaction flask, 0.48 g of silibinin was dissolved in 6 ml of DMF, 0.55 g of potassium carbonate was added, and stirred for 10 minutes to dissolve completely. 0.33 g of isopentenyl bromide was slowly added dropwise, stirred for 10 minutes, and then heated to reflux for 2 hours. Stand to cool, add 20 ml of distilled water, extract with ethyl acetate three times (10 ml each time), combine the organic layers, wash with 10 ml of distilled water, dry over anhydrous sodium sulfate, and concentrate under reduced pressure. The brownish-yellow crude product was obtained and subjected to column chromatography on 200-300 mesh silica gel (20 g), eluting with chloroform: ethyl acetate: acetic acid = 7:1:0.1 to obtain 220 mg of yellow crystal (I-c). Yield 35.6%.

[0040]Compound I-c name: 2-{2,3-dihydro-3-[4-(2-methyl-2-enebutyloxy)-3-methoxyphenyl]-2...

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PUM

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Abstract

The invention relates to a 7 and 20 dehydro-silybin dialky ether and preparation method and medicine use thereof. The compounds are capable of obviously preventing the lipid superoxide induced by the free radical from being generated; effectively protecting the injury rat adrenal pheochromocytoma cells PC12 due to hydrogen dioxide, namely with oxidation resistance injury protection function on thePC12 cells which simulate the cranial nerves; preventing the brain cells and the cranial nerves from being oxidized and controlling the neurodegenerative diseases such as senile dementia. In addition, the compounds have strong chelation on the ferrous ion. The pharmacodynamics result shows that: the compounds are anticipated to prepare the medicine for controlling the neurodegenerative diseases.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medical technology. Specifically, the present invention relates to the preparation method and pharmaceutical use of dehydrosilibinin di-ether substituted with alkyl at the 7-position and 20-position at the same time, and the compound has the activity of significantly inhibiting the formation of lipid peroxide induced by free radicals ; Potent against hydrogen peroxide-induced damage to rat adrenal pheochromoma PC12 cells, that is, to protect PC12 cells from simulating brain nerve cells against oxidation damage; It has a positive effect on the prevention and treatment of neurodegenerative diseases such as Alzheimer's disease. In addition, this type of compound also shows a strong chelation effect on ferrous ions, and the above pharmacodynamic results show that this type of dehydrosilibinin dialkyl ether compound can be expected to be used in the preparation of drugs for preventing and treating ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D407/04A61K31/357A61P25/28A61P25/14A61P25/16A61P21/00
Inventor 赵昱李海波夏从龙冯玉冰李校堃巫秀美郝小江曾苏施贵荣刘光明
Owner DALI UNIV
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