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Astilbin derivative and preparation method thereof

A technology for fucoside derivatives and compounds, applied in the field of astilbin derivatives and their preparation, can solve the problems of limited effect and the like, and achieve the effects of simple operation, reliable process and high yield

Inactive Publication Date: 2017-09-08
CHENGDU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Astilbin bioavailability can be improved by pharmacological approaches, but the effect is still very limited

Method used

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  • Astilbin derivative and preparation method thereof
  • Astilbin derivative and preparation method thereof
  • Astilbin derivative and preparation method thereof

Examples

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Effect test

preparation example Construction

[0041] A preparation method of astilbin derivatives, comprising the following steps:

[0042] A. Dissolving the raw material astilbin AB with 2 to 3 parts by weight in an organic solvent, the organic solvent is N,N-dimethylformamide, tetrahydrofuran or N,N-dimethylacetamide; Under the action, add 0.8~1.2 parts by weight of Bian chlorine or Bian bromine to carry out the substitution reaction, the temperature of the substitution reaction is 50~70°C, the reaction time is 5~7h, and the catalyst is 1~2 parts by weight of K 2 CO3, KI of 0.1-0.5 parts by weight. After the reaction, add water, extract and refine through the extractant to obtain the white solid intermediate AB-N-1; the extractant is ethyl acetate, dichloromethane or chloroform; the refinement is: the organic solvent The extracted organic phase was sequentially acid-washed, washed with water, dewatered, and spin-dried under reduced pressure to obtain white solid intermediate AB-N-1. Among them, dilute hydrochloric aci...

Embodiment 1

[0047] Embodiment 1, as figure 1 Shown, the preparation method of astilbin derivative, comprises the following steps:

[0048] A, the preparation of AB-N-1

[0049] Add 5.2g of AB raw material to the single-necked bottle, dissolve in 30mL DMF, add anhydrous K 2 CO 3 4g, KI 0.8g, add 6.86mL benzyl chloride, stir and react at 50°C for 7h. After the reaction, add 50mL water to the system, extract with chloroform (30mL×3), wash the organic phase with dilute HCl (20mL×3), wash with water (20mL×3), wash with saturated NaCl (20mL×3), and depressurize After spin-drying, 3.54 g of white solid was obtained, with a yield of 35%.

[0050] B. Preparation of AB-N-2

[0051] Add 0.24g of AB-N-1 to the reaction flask, dissolve it with 5mL of dichloromethane, add 0.15g of Boc-glycine, then add 0.05g of DMAP, 0.1g of DCC, and stir at 20°C for 20h. After the reaction, the reaction solution was suction filtered, the filtrate was spin-dried, 10 mL of water was added, extracted with dichloro...

Embodiment 2

[0056] Embodiment 2, as figure 1 Shown, the preparation method of astilbin derivative, comprises the following steps:

[0057] A, the preparation of AB-N-1

[0058] Add 4g of raw material AB to the single-necked bottle, dissolve in 20mL tetrahydrofuran, add anhydrous K 2 CO 3 3.5 g, KI 0.5g, add 10.97mL benzyl chloride, stir and react at 70°C for 5h. After the reaction, add 50mL water to the system, extract with ethyl acetate (30mL×3), wash the organic phase with dilute HCl (20mL×3), wash with water (20mL×3), wash with saturated NaCl (20mL×3), and depressurize After spin-drying, 4.05 g of white solid was obtained, with a yield of 38%.

[0059] B. Preparation of AB-N-2

[0060] Add AB-N-10.5g to the reaction flask, dissolve in 5mL THF, add 2.62g Boc-leucine, then add 0.05g DMAP, 0.1g DCC, and stir at 35°C for 18h. After the reaction, the reaction solution was suction filtered, the filtrate was spin-dried, 10 mL of water was added, extracted with chloroform (20 mL×3), the...

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Abstract

The invention discloses an astilbin derivative and a preparation method thereof. The derivative is AB-N-X or AB-H-X; the general formula of the AB-N-X is shown in the description, wherein R1 represents glycine, leucine, proline, serine or alanine; the general formula of the AB-H-X is shown in the description, wherein the representation of R2 is shown in the description. The preparation method comprises the steps: 1, dissolving astilbin organic solvent, and carrying out the replacement reaction with Bian chlorine or Bian bromine under catalyst, obtaining AB-N-1 after extraction and purification; 2, dissolving the AB-N-1 by adding organic solvent, adding natural amino acid or acid anhydride for reaction, and obtaining AB-N-2 or AB-H-1 after purification; 3, injecting hydrogen into the AB-N-2 or AB-H-1 under the catalysis of the catalyst, taking off protection to obtain the final product AB-N-X or AB-H-X. The astilbin derivative has high bioavailability; the preparation method is reliable in process, simple to operate, and high in yield.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to an astilbin derivative and a preparation method thereof. Background technique [0002] Astilbin is a dihydroflavonoid compound with two types of hydroxyl structures, polyphenol and rhamnose, and is an active ingredient in traditional Chinese medicines such as Smilax cocos and Saffron. Studies have shown that astilbin has a variety of significant biological activities, including inhibition of coenzyme A reductase, inhibition of aldose reductase, anti-edema and selective immunosuppression. Astilbin is easily soluble in organic solvents such as methanol and ethanol, and its water solubility is only 250ug / mL at 25°C, which is a very slightly soluble sample. The study on the pharmacokinetics of astilbin showed that the bioavailability of astilbin in rats was only 0.066%, and it was a compound with poor oral absorption. The bioavailability of astilbin can be improved by phar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07C07H1/00
CPCC07H17/07C07H1/00
Inventor 郭晓强李小红杨清赵卫赵琦周闯徐孝浪
Owner CHENGDU UNIV
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