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(E)3,5-di-methoxy-diphenylene-4'-0-phosphates (salt) and its preparing method, medicine composition and use

A technology of dimethoxystilbene and hydroxystilbene is applied in the field of stilbene derivatives, which can solve the problems of low biocompatibility and bioavailability, unfavorable vascular administration, low water solubility and the like, Achieving the effect of good biocompatibility, simple post-processing procedures and simple operation

Inactive Publication Date: 2009-12-09
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the compound has extremely low water solubility, low biocompatibility and bioavailability, and is not conducive to vascular administration

Method used

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  • (E)3,5-di-methoxy-diphenylene-4'-0-phosphates (salt) and its preparing method, medicine composition and use
  • (E)3,5-di-methoxy-diphenylene-4'-0-phosphates (salt) and its preparing method, medicine composition and use
  • (E)3,5-di-methoxy-diphenylene-4'-0-phosphates (salt) and its preparing method, medicine composition and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation of (E)-3,5-dimethoxystilbene-4'-O-phosphate disodium salt:

[0044] (E)-3,5-dimethoxy4'-hydroxystilbene 1.3g (0.005mol) was dissolved in 6mL CH 2 Cl 2 , then add POCl 3 2.6mL (0.028mol) was stirred well. Slowly add dropwise with 6mLCH 2 Cl 2 The dissolved 3.3 mL (0.024 mol) triethylamine was stirred for 6 hours at 25°C. After the reaction was completed, it was washed three times with an appropriate amount of water. The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain a yellow oily liquid, that is, the phosphorylated intermediate. 50 mL (0.015 mol) of NaOH solution with a concentration of 0.3 mol / L was added to the above phosphorylated intermediate concentrated solution, heated to 70-80° C. in an oil bath, and vigorously stirred to react for 8 hours. The insoluble matter in the reaction solution was removed by filtration, concentrated to dryness, and then recrystallized from a mixed solution of water and acetone to ob...

Embodiment 2

[0049] Preparation of (E)-3,5-dimethoxystilbene-4'-O-phosphate disodium salt:

[0050] (E)-3,5-dimethoxy-4'-hydroxystilbene compound 12.8g (0.05mol) was dissolved in 80mL CH 2 Cl 2 , then add POBr 3 20.5mL (0.2mol) was stirred evenly, and 16.0mL (0.2mol) pyridine and 40mL CH were slowly added dropwise 2 Cl 2 The solution was stirred at 25 °C for 4 hours. After the reaction was completed, it was washed three times with an appropriate amount of water. The organic layer was dried over anhydrous sodium sulfate, and concentrated to obtain a yellow oily liquid, which is a phosphorylated intermediate. 200 mL (0.20 mol) of 1 mol / L NaOH solution was added to the above phosphorylated intermediate concentrated solution, heated to 80° C. in an oil bath, and the reaction was stirred for 10 hours. The insolubles in the reaction solution were removed by filtration, concentrated to dryness, and then recrystallized with a mixed solution of ketone and acetone to obtain 17.0 g of a white s...

Embodiment 3

[0052] Preparation of (E)-3,5-dimethoxystilbene 4'-O-phosphate dipotassium salt:

[0053] (E)-3,5-dimethoxy-4'-hydroxystilbene compound 1.3g (0.005mol) was dissolved in 6mL CH 2 Cl 2 , then add POCl 3 2.6mL (0.028mol) was stirred well. Slowly add 1.4mL (0.02mol) trimethylamine and 6mL CH 2 Cl 2 The solution was stirred at room temperature for 8 hours. After the reaction was completed, it was washed three times with an appropriate amount of water. The organic layer was dried over anhydrous magnesium sulfate, and concentrated to obtain a yellow oily liquid, that is, the phosphorylated intermediate. 30 mL (0.015 mol) of 0.5 mol / L KOH solution was added to the above phosphorylated intermediate concentrated solution, heated to 50° C. in a water bath, and vigorously stirred to react for 6 hours. The insolubles in the reaction solution were removed by filtration, concentrated to dryness, and then recrystallized from a mixed solution of water and acetone to obtain 1.5 g of a w...

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Abstract

The invention discloses (E)-3,5-dimethoxystilbene-4'-O-phosphate (salt) and its preparation method, pharmaceutical composition and its preparation for reducing blood fat, blood sugar, Application of antifungal drugs. The (E)-3,5-dimethoxystilbene-4'-O-phosphate (salt) of the present invention is obtained through (E)-3,5-dimethoxy-4'-hydroxy di Styrene reacts with a phosphorylating reagent at 10-70°C in the presence of an acid-binding agent to obtain a phosphorylated intermediate; then in an alkaline solution, heat the phosphorylated intermediate to 50-100°C to react and purify prepared afterwards. The compound of the present invention and its pharmaceutical composition have therapeutic effects such as lowering blood fat, lowering blood sugar, and antifungal; the preparation method of the compound is simple in operation, low in cost, high in yield, adopts an environmentally friendly solvent, has little environmental pollution, and has mild reaction conditions. The post-processing procedure is simple.

Description

technical field [0001] The invention relates to a stilbene derivative, in particular to a (E)-3,5-dimethoxystilbene-4'-0-phosphate (salt), a preparation method and a pharmaceutical composition thereof and its application in the preparation of hypolipidemic, hypoglycemic and antifungal drugs. Background technique [0002] (E)-3,5-dimethoxy-4'-hydroxystilbene (namely Pterostilbene, Pterostilbene), its structure is shown in formula (1): [0003] [0004] Formula 1) [0005] It is a homologue of resveratrol with a trans-stilbene skeleton structure and is an important active ingredient in grapes, blueberries, dried blood products and the Indian anti-diabetic herb "Bijasar" (Inter J Biochem & Cell Bio 2005, 37, 1709) , also exists in Chinese stegophylla, and its pharmacological action is not only partially similar to resveratrol (J Agric Food Chem 2002, 50, 3453), but also has strong antifungal activity (Chinese Herbal Medicine 2001, 32 , 241), cancer chemopreventive activit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/12A61K31/661A61P3/06A61P3/10A61P31/10
Inventor 邹永甄永刚黄文明林慧贞魏文陈爱民
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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