Preparation method and applications of forsythoside glucuronic acid derivative

A technology of glucuronic acid and forsythiatin, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problem of forsythiatin molecular instability, easy to change molecular configuration, and easy to be oxidized and other problems, to achieve the effect of convenient source of raw materials, easy quality control, and improved selectivity

Active Publication Date: 2016-12-07
富力
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The molecule of forsythiatin is unstable, easily oxidized, a...

Method used

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  • Preparation method and applications of forsythoside glucuronic acid derivative
  • Preparation method and applications of forsythoside glucuronic acid derivative
  • Preparation method and applications of forsythoside glucuronic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] 1. Preparation of forsythiatin-organic base complex

[0065] Add forsythiatin (4g, 10.75mmol) into dry anhydrous dichloromethane (180ml) at a temperature of 10°C, stir to dissolve and add organic base N,N-diisopropylethylamine 11.26mL (64.5mmoL), stirred for 10 minutes, carried out the hydroxyl activation reaction, and prepared the forsythiatin-organic base complex solution for later use, and the molar ratio of forsythiatin to organic base was 1:6;

[0066] In the process of the hydroxyl activation reaction in the present invention, controlling the reaction temperature at 0-20°C is applicable to the present invention, and the embodiment of the present invention takes 10°C as an example for illustration. In the present invention, except for the molar ratio of forsythiatin and organic base being 1:6, other molar ratios of 1:5-8 are applicable to the present invention. The embodiment of the present invention is described by taking 1:6 as an example.

[0067] The hydroxyl...

Embodiment 2

[0086] Except that the organic base 1,8-diazabicycloundec-7-ene (9.63 mL, 64.5 mmol) was added in step 1; the glycosyl donor in step 2 was 2,3,4-tri-O- The mass of benzoyl α-D bromoglucopyranose methyl ester is 43.89g (75.25mmoL), and the molar ratio of glycosyl donor to forsythialin is 7:1; catalyst silver carbonate (124.5g, 0.4515mol), except that the molar ratio of the catalyst to the sugar group donor was 6:1, the rest were the same as in Example 1 to obtain a white solid (compound 2, 3g), with a total yield of 79.8%.

[0087] Compound 2 is a white solid, soluble in water and ethanol. Develop on a TLC plate (chromatographic solution is chloroform / methanol 3:1, Rf is 0.4) and then spray 10% H 2 SO 4 -Ethanol reagents are purple in color.

[0088] In the ESI-MS spectrum of compound 2, m / z[M-Na] - It is 547.18210 and the molecular weight is 570.52277.

[0089] Compound 2 1 H-NMR, 13 C-NMR, IR are the same as compound 1 prepared in Example 1.

[0090] According to ESI-...

Embodiment 3

[0092] 1. Preparation of forsythiatin-organic base complex

[0093] Add forsythiatin (4g, 10.75mmol) into dry anhydrous dichloromethane (180ml) at a temperature of 0°C, stir to dissolve and add organic base 1,8-diazabicycloundec Carb-7-ene 9.63mL (64.5mmol), stirred for 20 minutes, carried out hydroxyl activation reaction, prepared forsythiatin-organic base complex solution for subsequent use;

[0094] 2. Glycosidation reaction

[0095] 2-1) 6.4g (16.125mmoL) of 2,3,4-tri-O-acetyl α-D bromoglucopyranose methyl ester and 17.78g (64.5 mmoL) was dissolved in dichloromethane, stirred uniformly to obtain glycosidation reagent;

[0096] 2-2) Add the forsythiatin-organic base complex solution into the glycosylation reagent while stirring at 0°C and nitrogen atmosphere, then heat up to 20°C, and keep the temperature at 20°C , carry out glycosylation reaction 10h, make glycosylation reaction mixture;

[0097] 3. Deacylation reaction

[0098] Under stirring, the glycosidation react...

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Abstract

The present invention provides a preparation method, antivirus applications and the like of a forsythoside glucuronic acid derivative represented by the following formula, wherein R is H, Me, Na<+>, K<+>, and the like.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular, the invention relates to a forsythiaside glucuronic acid derivative and a preparation method thereof, as well as the antiviral pharmacological effect of this kind of derivative. Background technique [0002] Forsythiatin, the glycogen part of forsythin, also known as forsythiagenin, is the main active ingredient of Forsythia genus Forsythia in Oleaceae. Its structure is shown in the following formula. Modern pharmacological studies have shown that forsythia Artholiline has anti-virus, anti-oxidation, lowering blood fat, scavenging free radicals, antibacterial, anti-tumor, anti-inflammatory and other effects. [0003] [0004] The molecule of forsythiatin is unstable, easily oxidized, and the molecular configuration is easily changed in an acidic environment. Through the research on the metabolism of forsythin simulated by intestinal bacteria in rats, it is found that it is ea...

Claims

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Application Information

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IPC IPC(8): C07H15/26C07H1/00A61P31/12A61P31/16A61P31/22
CPCA61P11/00A61P31/12A61P31/14A61P31/16A61P31/20A61P31/22C07H1/00C07H15/26
Inventor 樊宏宇富力姜人武王凯乾
Owner 富力
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