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Isopentenyl-oxyl substituted dehydrogenized silybin ether and preparation method and application thereof

A technology of isopentenyloxy and silibinin, which is applied in the field of preparation of dehydrosilibinin ether derivatives, can solve problems such as damage and changes in the biphospholipid layer of cell membranes, and achieves a simple method and free radical scavenging , the effect of protecting brain nerve cells

Inactive Publication Date: 2010-06-09
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 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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  • Isopentenyl-oxyl substituted dehydrogenized silybin ether and preparation method and application thereof
  • Isopentenyl-oxyl substituted dehydrogenized silybin ether and preparation method and application thereof
  • Isopentenyl-oxyl substituted dehydrogenized silybin ether and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 : Compound I is the preparation of 7-prenyloxy substituted deoxysilibinin ether

[0024]

[0025] In a dry reaction flask, 0.241 g of silibinin was dissolved in 5 ml of DMF, 0.276 g of potassium carbonate was added, and stirred for 10 minutes to dissolve completely. 50 mg of isopentenyl bromide was slowly added dropwise, stirred for 5 minutes, and reacted at 75°C for 1 hour. 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. A light yellow crude product was obtained, which was subjected to 200-300 mesh silica gel (7 g) column chromatography, eluting with petroleum ether: ethyl acetate: acetic acid = 5:1:0.1 to obtain 39.3 mg of a light yellow solid. Yield 14.3%.

[0026] Compound I: 2-[2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxane-6-]- 3...

Embodiment 2

[0031] Example 2 : Activity test of compound I for scavenging diphenylpicrylhydrazyl free radicals (1,1-diphenyl-2-picrylhydrazyl, DPPH) in vitro

[0032] 2.1 Test principle: DPPH is an aryl radical that can exist stably in vitro and is widely used to evaluate the antioxidant activity of compounds. free radical scavenging ability. DPPH is easily soluble in methanol, the solution is dark purple, and has a maximum absorption at 517nm. If the free radical is captured by the compound to be tested, the absorbance at 517nm will decrease. The more the absorbance decreases, the greater its ability to scavenge DPPH free radicals Also stronger.

[0033] 2.2 Experimental materials and samples

[0034] 2.2.1 Experimental reagents:

[0035] 2.2.1.1 Phenazine methosulfate (PMS), nitroblue tetrazolium (NBT), and phenanthrozine (ferrozine) were purchased from Sigma;

[0036] 2.2.1.2 Silybin was purchased from Liaoning Panjin Tianyuan Pharmaceutical Co., Ltd., with a purity of 98% by HPL...

Embodiment 3

[0054] Example 3 : formula (I) compound I to hydrogen peroxide H 2 o 2 Protective activity test of induced PC12 cell injury

[0055] 3.1 Experimental materials and samples

[0056] 3.1.1 Cells: Rat adrenal pheochromoma PC12 cells were purchased from Shanghai Cell Institute, Chinese Academy of Sciences.

[0057] 3.1.2 Experimental reagents:

[0058] 3.1.2.1 Hydrogen peroxide (H 2 o 2 ), nitrobluetetrazolium (NBT), phenanthrozine (ferrozine) were purchased from Sigma Company;

[0059] 3.1.2.2 Silybin was purchased from Liaoning Panjin Tianyuan Pharmaceutical Co., Ltd., and its purity was 98% by HPLC.

[0060] 3.1.2.3 Tris base, DMEM medium was purchased from Gibco;

[0061] 3.1.2.4 MTT was purchased from Amresco;

[0062] 3.1.2.5 Calf serum was purchased from Hangzhou Sijiqing Bioengineering Materials Co., Ltd.;

[0063] 3.1.2.6 Penicillin and streptomycin are produced by Shijiazhuang Pharmaceutical Group Co., Ltd.;

[0064] 3.1.2.7 Other reagents are domestic analyt...

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PUM

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Abstract

The invention relates to Isopentenyl-oxyl substituted dehydrogenized silybin ether and the preparation method and the application thereof. The compound has the activity of eliminating extracorporeal extracorporeal 1-diphenyl-2-picrylhydrazyl radical, the activity of obviously inhibiting the generation of lipid peroxide induced by radical and the function of powerfully preventing the damage of therat adrenal pheochromocytoma PC12 cells due to the hydrogen peroxide, i.e. the function of preventing the oxidative damage of the PC12 cells simulating the brain nerve cells, thereby playing a positive role in preventing the brain cell tissue oxidation and brain never oxidation and preventing and treating the senile dementia and other neurodegenerative diseases. The pharmacodynamic result shows that 7-site substituted dehydrogenized silybin ether can be expectantly used for preparing the medicament for preventing and treating 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 a preparation method and pharmaceutical use thereof of 7-isopentenyloxy substituted dehydrosilibinin ether derivatives, the compound has the activity of scavenging free radicals in vitro; significantly inhibits free radical-induced Lipid peroxide generation activity; powerful anti-hydrogen peroxide-induced damage to rat adrenal pheochromoma PC12 cells, that is, to protect PC12 cells from simulating brain nerve cells against oxidative damage; it shows that it can protect brain cells against Oxidation and brain nerve anti-oxidation, prevention and treatment of neurodegenerative diseases such as Alzheimer's disease have positive effects. The above pharmacodynamic results show that the dehydrosilibinin ether compound can be expected to be used in the preparation of drugs for preventing and treating neurodegenerative diseases. Bac...

Claims

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Application Information

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IPC IPC(8): C07D407/04A61K31/357A61P25/28A61P25/14A61P25/16A61P21/00A61P39/06
Inventor 赵昱杨雷香肖怀龚景旭巫秀美郝小江曾苏何正春刘光明
Owner DALI UNIV
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