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Dehydrogenated silibinin substituted by meta-chlorobenzene formoxyl, preparation method and pharmaceutical applications thereof

A technology of dehydrosilibinin and chlorobenzoyl, which is applied in the field of medicine, can solve the problems of water solubility and bioavailability limiting the drug market, etc., and achieve the effect of short steps, simple method and high yield

Inactive Publication Date: 2009-11-11
WENZHOU MEDICAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Silibinoids have definite antioxidant activity, but some deficiencies in water solubility and bioavailability limit the market of this drug

Method used

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  • Dehydrogenated silibinin substituted by meta-chlorobenzene formoxyl, preparation method and pharmaceutical applications thereof
  • Dehydrogenated silibinin substituted by meta-chlorobenzene formoxyl, preparation method and pharmaceutical applications thereof
  • Dehydrogenated silibinin substituted by meta-chlorobenzene formoxyl, preparation method and pharmaceutical applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1 : Formula (I) compound m-chlorobenzoic acid [3-(4-hydroxy-3-methoxyphenyl)-6-(3,5,7-trihydroxy-4-oxo-benzopyran-2 )-2,3-dihydro-1,4-benzodioxane-2]-methyl ester

[0016]

[0017] 1.12, Preparation of 3-dehydrosilibinin:

[0018] Add 1.02 grams of silybin, 10 grams of potassium acetate, and 50 milliliters of glacial acetic acid into the dry reaction bottle, and then add 50 milliliters of glacial acetic acid dissolved in 1 gram of iodine under ice cooling. Heat to reflux for 5 hours. After cooling down, 50 ml of ice water was added, extracted with ethyl acetate (20 ml x 4 times), the organic layers of the extracts were combined, washed with water, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to obtain a reddish-brown solid, which was added to 50 ml of ethanol solution containing 6 ml of hydrochloric acid. Heat to reflux for 3 hours. After lowering the temperature, a yellow solid was precipitated, and recrystall...

Embodiment 2

[0028] Example 2 : Formula (I) compound m-chlorobenzoic acid [3-(4-hydroxy-3-methoxyphenyl)-6-(3,5,7-trihydroxy-4-oxo-benzopyran-2 )-2,3-dihydro-1,4-benzodioxane-2]-methyl ester to hydrogen peroxide H 2 o 2 Protective activity test of induced PC12 cell injury

[0029] 2.1 Experimental materials and samples

[0030] 2.1.1 Cells: rat adrenal pheochromocytoma (PC12) cells were purchased from Shanghai Institute of Cells, Chinese Academy of Sciences.

[0031] 2.1.2 Experimental reagents:

[0032] 2.1.2.1 Hydrogen peroxide (H 2 o 2 ), nitroblue tetrazolium (NBT), and phenanthrozine (ferrozine) were purchased from Sigma;

[0033] 2.1.2.2 Quercetin (quercetin) was provided by the Laboratory of Traditional Chinese Medicine and Natural Medicine, School of Pharmacy, Zhejiang University (purity: 99%); Silybin (Silybin) was purchased from Panjin Tianyuan Pharmaceutical Co., Ltd., Liaoning, and detected by HPLC 98% purity.

[0034] 2.1.2.3 Tris base, DMEM medium was purchased from...

Embodiment 3

[0061] Example 3 : Formula (I) compound m-chlorobenzoic acid [3-(4-hydroxy-3-methoxyphenyl)-6-(3,5,7-trihydroxy-4-oxo-benzopyran-2 )-2,3-dihydro-1,4-benzodioxane-2]-methyl ester inhibits the activity of free radical-induced lipid peroxide generation

[0062] 3.1 Experimental principle: Lipid peroxidation is the product of free radicals acting on polyunsaturated fatty acids, and the content is positively correlated with the generation of free radicals. Because the body has anti-oxidant enzymes and non-enzyme protection, free radicals are continuously generated was continuously removed. With the growth of age, the antioxidants in the body continue to decline, the ability to scavenge free radicals gradually weakens, the lipid peroxidation increases, and the lipid peroxidation products increase. Therefore, the determination of the anti-lipid peroxidation effect of samples is one of the important indicators for screening anti-oxidation and anti-aging drugs. Vitamin C-Fe was use...

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Abstract

The invention relates to a dehydrogenated silibinin substituted by meta-chlorobenzene formoxyl, a preparation method and pharmaceutical applications thereof, in particular to a preparation method and applications of 2,3-dehydrogenated silibinin substituted by 23-site meta-chlorobenzene formoxyl. The compound has applications of inhibiting activity of production of lipid superoxide induced by free radical and can be expectedly used for preparing medicine for prevention and treatment of acute and chronic liver damage, hepatitis and cerebral atherosclerosis which are caused by the lipid superoxide. The compound further shows very strong resistance for PC12 cell damage caused by free radical and can be expectedly developed into medicine for protecting cranial nerve from oxidation and preventing and treating senile dementia. Besides, the compound has strong xanthine oxidase activity inhibition and can be expectedly developed into medicine for preventing and treating diseases caused by xanthine oxidase.

Description

technical field [0001] The invention relates to the technical field of medicine. Specifically, the present invention relates to a preparation method of 2,3-dehydrosilibinin ester derivatives substituted by m-chlorobenzoyl group at the 23-position and its medical application. The activity of oxidation generation can be expected to develop into the prevention and treatment of diseases caused by or related to free radicals, including inflammation, autoimmune diseases, sequelae of radiation therapy, tumors, myocardial ischemia, cardiac hypertrophy, aging, allergies, atherosclerosis Medicines for other diseases. The compound also exhibits a strong anti-free radical-induced damage to rat adrenal pheochromocytoma (PC12) cells, that is, it has an anti-oxidative damage protection effect on PC12 cells that simulate brain nerve cells, indicating that it can protect brain cell tissue Anti-oxidation and anti-oxidation of cranial nerves have positive effects on prevention and treatment of...

Claims

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Application Information

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IPC IPC(8): C07D407/04A61K31/357A61P39/06A61P25/28A61P1/16A61P9/10A61P43/00A61P19/06
Inventor 李校堃冯玉冰黄可新龚景旭杨雷香伍义行巫秀美瞿佳赵昱曾苏
Owner WENZHOU MEDICAL UNIV
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