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Xylogen like flavonoid compounds, method of preparing the same and pharmaceutical use

A compound and lignin technology, applied in the field of medicine, can solve the problems of water solubility and bioavailability limiting the drug market, and achieve the effects of inhibiting xanthine oxidase activity, low human toxicity, and high yield

Inactive Publication Date: 2009-08-19
WENZHOU MEDICAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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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  • Xylogen like flavonoid compounds, method of preparing the same and pharmaceutical use
  • Xylogen like flavonoid compounds, method of preparing the same and pharmaceutical use
  • Xylogen like flavonoid compounds, method of preparing the same and pharmaceutical use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 : Compound I-a is (±)-2-[2,3-dihydro-2-(3-methoxy-4-hydroxyphenyl)-3-hydroxymethyl-1,4 benzodioxane- 5] Preparation of -2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one

[0027]

[0028] 1.1 Preparation of starting material A:

[0029] starting material A

[0030]Dissolve 4.8 g of 2,3-dihydroxybenzaldehyde in 30 ml of acetone, stir for 10 minutes, add 17.5 g of potassium carbonate, then dropwise add 6 ml of chloromethyl ether, heat to reflux for 1 hour, filter, and concentrate the filtrate to obtain 7.0 g of yellow oil , used directly in the next reaction.

[0031] 1.2 Preparation of starting material B:

[0032] starting material B

[0033] 2.6 grams of sodium hydride in 40 milliliters of DMF was cooled in an ice-water bath, and a mixed solution of 5.6 grams of 2,4,6-trihydroxyacetophenone in 60 milliliters of benzene and 7.0 milliliters of DMF was added dropwise under nitrogen protection, and cooled in an ice bath 9.0 ml of chloromethyl ether ...

Embodiment 2

[0045] Example 2 : Compound I-b is (±)-2-[2,3-dihydro-2-(3-benzyloxy-4-hydroxyphenyl)-3-hydroxymethyl-1,4 benzodioxane- 5] Preparation of -2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one

[0046]

[0047] According to the synthesis method described in Example 1, from (±)-2-(2,3-dihydroxyphenyl) 2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyridine The coupling reaction between pyran-4-one and 3-benzyloxy-4-hydroxycinnamyl alcohol finally obtained 36 mg of compound I-b. R f (chloroform / methanol / ethyl acetate / acetone / acetic acid=11:0.5:1:1:0.1): 0.29; electrospray mass spectrometry ESI-MS: 557 (M-1) + .

Embodiment 3

[0048] Example 3 : Compound I-c is (±)-2-[2,3-dihydro-2-(3,5-dimethoxy-4-hydroxyphenyl)-3-hydroxymethyl-1,4 benzodiox Preparation of Hexacyclo-5]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one

[0049]

[0050] According to the synthesis method described in Example 1, from (±)-2-(2,3-dihydroxyphenyl) 2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyridine The coupling reaction between pyran-4-one and 3,5-dimethoxy-4-hydroxycinnamyl alcohol finally obtained 26 mg of compound I-c. R f (chloroform / methanol / ethyl acetate / acetone / acetic acid=11:0.5:1:1:0.1): 0.24; electrospray mass spectrometry ESI-MS: 511 (M-1) + .

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Abstract

The invention relates to a series of lignin flavonoid compounds as well as a preparation method and drug use thereof, in particular to a preparation method of a series of beta-cyclodioxane lignin flavonoild compounds and use thereof for preparing antioxidant drugs. The compounds have strong activity of inhibiting xanthine oxidase, and can be expected to be developed into drugs for preventing and treating gout diseases resulting from the xanthine oxidase. The compounds also exhibit strong effects of protecting against PC12 cell injury resulting from free radicals, and can be expected to be developed into drugs for preventing and treating senile dementia. The compounds also have the effects of protecting against free radicals in vitro, protecting hepatic cells and relieving injury resulting from hydrogen peroxide, thus being capable of being expected to be developed into drugs for treating various diseases resulting from the free radicals, especially the use of drugs for preventing and treating liver injury.

Description

technical field [0001] The present invention relates to the technical field of medicine, specifically, the present invention relates to a medicine that can inhibit xanthine oxidase, protect brain nerve cells against oxidation damage, prevent and treat senile dementia, and prevent and treat liver cell damage caused by free radical damage. The preparation method of the dihydroflavonol lignin compound of B-ring dioxane and its medical application. Pharmacological tests show that the compound has strong inhibitory activity of xanthine oxidase, and can be expected to be developed into a drug for preventing and treating diseases caused by xanthine oxidase, including gout. In addition, the compound also showed a strong anti-free radical-induced damage to rat adrenal pheochromoma cells, that is, PC12 cells, that is, it has an anti-oxidative damage protection effect on PC12 cells that simulate brain nerve cells, indicating that it has a protective effect on the protection of brain cell...

Claims

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Application Information

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IPC IPC(8): C07D407/04A61K31/357A61P39/06A61P37/00A61P35/00A61P9/10A61P25/28A61P1/16A61P19/06A61P43/00
Inventor 李校堃汪峰黄可新龚景旭冯玉冰杨雷香王晓雨巫秀美瞿佳曾苏赵昱
Owner WENZHOU MEDICAL UNIV
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