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Flavone lignose compound, and preparation and pharmaceutical use thereof

A technology of flavonoid lignin and compound, applied in the field of medicine, can solve the problems of insufficient water solubility and bioavailability, restricting the drug market, etc., and achieve the effects of being beneficial to large-scale production, easy to obtain raw material sources, and huge social benefits

Inactive Publication Date: 2009-07-08
WENZHOU MEDICAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] 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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  • Flavone lignose compound, and preparation and pharmaceutical use thereof
  • Flavone lignose compound, and preparation and pharmaceutical use thereof
  • Flavone lignose compound, and preparation and pharmaceutical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 : Compound I-a is (±)-trans-6-hydroxyl 2-hydroxymethyl-3-(4-hydroxyphenyl)-9-phenyl-2,3-dihydro-[1,4]dioxane Preparation of [2,3-h]benzopyran-7-one

[0032]

[0033] 1.1 Put 2.28 grams of 5,7-dihydroxyflavone into a dry nitrogen-protected reaction flask, dissolve it in 3.15 grams of potassium hydroxide aqueous solution, add 0.322 grams of tetrabutylammonium bromide, and add the dissolved 3 g of potassium persulfate in 90 ml of aqueous solution, after the dropwise addition, was stirred for 2 hours, the ice bath was removed, and left overnight at room temperature. Use 1N hydrochloric acid to adjust the pH value to 5, stir, filter the precipitated khaki solid, add 22.5 ml of concentrated hydrochloric acid and 2.25 g of sodium sulfite to the filtrate, heat and boil for 10 minutes, let stand to cool, filter, wash the filter cake with water until neutral, and dry to obtain 1.07 g of brown-yellow crude product was recrystallized from absolute ethanol to obtain 0...

Embodiment 2

[0036] Example 2 : Compound I-b is (±)-trans-6-hydroxyl 2-hydroxymethyl-3-(3-bromo-4-hydroxyl-5-methoxyphenyl)-9-phenyl-2,3-dihydro Preparation of -[1,4]dioxane[2,3-h]benzopyran-7-one

[0037]

[0038] 2.1 Preparation of 5,7,8-trihydroxyflavone, the method is the same as described in 1.1 in Example 1.

[0039] 2.2 Put 0.22 g of 5,7,8-trihydroxyflavone, 0.423 g of 3-bromo-4-hydroxy-5-methoxy-cinnamyl alcohol and 0.56 g of silver oxide into a reaction flask protected by dry nitrogen, and inject 8 ml of anhydrous Acetone and 24 ml of anhydrous benzene were incubated at 50-60°C for 15 hours, filtered, concentrated mother liquor, and separated by column chromatography on silica gel (200-300 mesh, 20 g) (chloroform / methanol=9:1-2:1) , to obtain 0.193 g of light yellow needle-like crystals, with a yield of 45%.

[0040] (±)-trans-6-hydroxyl-2-hydroxymethyl-3-(3-bromo-4-hydroxyl-5-methoxyphenyl)-9-phenyl-2,3-dihydro-[1 , 4] dioxane [2,3-h] benzopyran-7-one (I-b): R f (chlorof...

Embodiment 3

[0046] Example 3 : Compound I-b is (±)-trans-6-hydroxyl 2-hydroxymethyl-3-(3-bromo-4-hydroxyl 5-methoxyphenyl)-9-phenyl-2,3-dihydro- [1,4]dioxane[2,3-h]benzopyran-7-one to hydrogen peroxide H 2 o 2 Protective effect of induced PC12 cell injury

[0047] 3.1 Experimental materials and samples

[0048] 3.1.1 Cells: Rat adrenal pheochromoma cells (PC12) were purchased from Shanghai Institute of Cells, Chinese Academy of Sciences.

[0049] 3.1.2 Experimental reagents:

[0050] 3.1.2.1 Hydrogen peroxide (H 2 o 2 ), nitroblue tetrazolium (NBT), and phenanthrozine (ferrozine) were purchased from Sigma;

[0051] 3.1.2.2 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.

[0052] 3.1.2.3 Tris base, DMEM medium was purchased from Gibco;

[0053] 3....

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PUM

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Abstract

The invention relates to scutellaprostin compounds, methods for preparing the same and pharmaceutical uses of the same. Particularly, the invention relates to preparation methods and pharmaceutical uses of A cyclo-dioxane scutellaprostin compounds capable of inhibiting the activities of xanthine oxidase, protecting brain nerve cells from oxidative damages and preventing and treating senile dementia. The compounds have strong inhibition effect on the activities of the xanthine oxidase and are expected to be used to prepare drugs or pharmaceutical compositions for preventing and treating diseases such as gout caused by the xanthine oxidase. The compounds have strong anti-oxidative damage and protective effects on PC12 cells simulating brain nerve cells and are expected to be used to prepare drugs or pharmaceutical compositions for protecting brain nerves, preventing aging and preventing and treating senile dementia.

Description

technical field [0001] The invention relates to the field of medical technology, specifically, the invention relates to a class of A-ring dioxane flavonoid lignin that can inhibit xanthine oxidase, protect brain nerve cells from oxidative damage, and prevent and treat senile dementia Preparation method and medical use of similar compounds. The pharmacological tests carried out in the present invention show that the compound has a strong activity of inhibiting 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 exhibited a strong anti-oxidative damage protection effect on rat adrenal pheochromoma cell PC12 cells caused by free radicals, 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...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61K31/357A61P25/28A61P19/06A61P39/06A61P43/00
Inventor 黄可新龚景旭李校堃汪峰杨雷香白骅巫秀美赵昱瞿佳
Owner WENZHOU MEDICAL UNIV
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