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Dehydrosilibinin diester derivatives, preparation method and use thereof

A technology of dehydrogenated water and derivatives, applied in the field of organic chemistry and medicinal chemistry, can solve the problems of limited drug market, insufficient water solubility and bioavailability

Inactive Publication Date: 2010-03-31
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Silybin compounds have definite curative effect, but the market of this drug is limited due to some shortcomings in water solubility and bioavailability

Method used

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  • Dehydrosilibinin diester derivatives, preparation method and use thereof
  • Dehydrosilibinin diester derivatives, preparation method and use thereof
  • Dehydrosilibinin diester derivatives, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Compound I-1 (2-[2,3-dihydro-3-(4-N,N-diethylcarbamoylmethoxy-3-methylhydrogenphenyl)-2-hydroxymethyl-1 ,4-benzodioxane-6-]-7-(4-N,N-diethylcarbamoylmethoxy-3-methoxyphenyl)-3,5,-dihydroxy- 4H-1-benzopyran-4-one) preparation:

[0030]

[0031]2.2 grams of compound I-a (silibinin) were dissolved in 15 milliliters of N,N-dimethylformamide, 1 gram of potassium carbonate and 0.15 grams of potassium iodide were added, and 0.67 grams of N,N-diethylchloroacetamide was added under stirring , stirred overnight at room temperature, the reactant was poured into 30 ml of ice water, and the yellow bag precipitate was precipitated, extracted with ethyl acetate, washed with saturated brine after combining the extracts, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a yellow solid. 1.2 g of yellow powder was obtained by column chromatography with a yield of 60%.

[0032] Rf (chloroform: methanol = 50: 1) = 0.1; 1 H NMR (400MHz, deuterated di...

Embodiment 8

[0044] Embodiment 8: Compound I-8 ([2-[2,3-dihydro-3-(4-ethoxyformylmethoxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzo Dioxane-6-]-2,3-dihydro-7-(4-ethoxyformylmethoxy-3-methoxyphenyl)-3,5,-dihydroxy-4H-1- The preparation of benzopyran-4-one]):

[0045]

[0046] According to the same method as in Example 1, the raw material ethyl chloroacetate was used instead of N, N-diethyl chloroacetamide to obtain compound I-8: Rf (chloroform: ethyl acetate: formic acid=25:1:0.25)=0.10 ; 1 H NMR (400MHz, deuterated dimethylsulfoxide): 1.23(t, J=7.2Hz, 3H, CH3), 1.31(t, J=7.2Hz, 3H, CH3), 3.58(m, 1H, 9'a ), 3.86(m, 1H, H-9'b), 4.13(m, 1H, H-8'), 4.20(q, J=7.2Hz, 2H, CH2CH3), 4.28(q, J=7.2Hz, 2H, CH2CH3), 4.28 (m, 1H, H-8'), 4.67 (s, 2H, H-9), 4.82 (s, 2H, OCH2CO), 5.99 (d, J=8.0Hz, 1H, OCH2CO) , 6.35(s, 1H, H-6), 6.41(s, 1H, H-8), 6.96-8.01(m, 6H, Ar-H), 12.50(s, 1H, 5-OH); ESI-MS 653[M+1] + .

[0047]The compounds of formula I have various important biological activities. The p...

Embodiment 2

[0059] Pharmacological embodiment 2: Activity Test of Compound I-2 in Vitro Scavenging Diphenylpicrylhydrazyl (1,1-diphenyl-2-picrylhydrazyl, DPPH)

[0060] The methanol solution of DPPH has a strong absorption value at 517nm. When it is reduced by antioxidants, the absorption value decreases. The lower the absorbance, the stronger the antioxidant effect. In a 250 μL reaction system, 25 μL of compound I-2 with a concentration of 40 μg / mL, 40 μL of methanol solution of DPPH (0.4 mg / mL) and 185 μL of methanol solution were contained, and the absorbance was measured at 517 nm after reacting in a water bath at 37 °C for 30 minutes. The methanol solution of DPPH and the same concentration of quercetin were used as negative and positive controls, respectively. The test results are shown in Table 3.

[0061] Table three

[0062]

[0063]

[0064] The test results show that compound I-2 has a certain DPPH free radical scavenging effect, but at the same concentration, its sca...

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Abstract

The present invention relates to an anti-free radical oxidation, liver-protective, senile dementia preventing and anti-aging active dehydrogenation silybin double-ester derivative and the related medicinal salt or solvent compound. The invention also relates to the preparation method for the compound on the formula 1, as well as the related medication compounds and the curatorial uses. The compound of the invention can protect the liver cells of a rat liver cell injury in vitro model, which can be expected to prevent liver damage in drug use; the compound of the invention is provided with thebiological activities of in vitro removing superoxide anion free radicals and diphenyl-benzyl-hydrazine free radicals, and restraining generation of grease peroxide induced by free radicals. The compound can strongly confront the PC12 cells damage caused by free radicals, which can be expected to prevent various diseases caused by free radicals in drug use.

Description

technical field [0001] The invention belongs to the field of organic chemistry and medicinal chemistry, in particular, the invention relates to a preparation method and application of a class of dehydrosilibinin diester derivatives. Such compounds are obtained through total synthesis and semi-synthesis methods. The present invention screens the hepatocyte injury protection activity of the series of compounds on the hydrogen peroxide-induced primary liver cell injury model of rat suckling rats. This type of compound has been found to protect liver cells and promote the repair of liver cells. The present invention has tested the antioxidant free radical activity of this type of compound, and found that it has the activity of scavenging superoxide anion free radicals in vitro, scavenging diphenylpicrylphenylhydrazine free radicals, and inhibiting the formation of lipid peroxides induced by free radicals . The above activities indicate that this type of compound can be expected...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61P39/06C07D407/04A61P25/28A61P1/16A61K31/357
Inventor 赵昱龚景旭汪峰冯玉冰白骅
Owner ZHEJIANG UNIV
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