Epigallocatechin gallate glycoside derivative and application thereof

A technology of epigallocatechin and glycoside derivatives is applied in the application field of preparing anti-cancer preparations, and can solve the problems of low bioavailability, insufficient stability, affecting the efficacy of cancer treatment and the like

Inactive Publication Date: 2018-08-31
YUNNAN AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

EGCG has been shown to have low bioavailability and insufficient stability during experiments, which affects its utility in cancer therapy

Method used

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  • Epigallocatechin gallate glycoside derivative and application thereof
  • Epigallocatechin gallate glycoside derivative and application thereof
  • Epigallocatechin gallate glycoside derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The synthesis process of the present invention is as figure 2 shown.

Embodiment 2

[0047] Preparation of compound 4"-β-glucoside epigallocatechin gallate (Compd.1) (steps 1, 2, and 3):

[0048] first step: Preparation of 1,2,3,4,6-peracetyl-β-glucose:

[0049] Dissolve D-glucose (3.6g, 20mmol) in acetic anhydride (8.3mL, 70mmol), heat and stir in an oil bath preheated to 100°C, then slowly add anhydrous sodium acetate (2.4g, 60mmol ), the reaction was terminated after heating to reflux at 100° C. for 2 h. After the reaction was completed, add water to dilute the reaction solution and extract three times with saturated sodium bicarbonate solution, then extract three times with water, extract the organic phase, dry over anhydrous sodium sulfate and concentrate under reduced pressure to obtain a crude product purified by silica gel chromatography (elution condition: petroleum ether / ethyl acetate=1:1). 2.62 g of compound 1,2,3,4,6-peracetyl-β-glucose was obtained with a yield of 72%. 1 H-NMR (CDCl 3 ,400MHz)δ5.70(d,1H,J=8.4Hz,C1-H),5.74(t,1H,J=9.2Hz,C 3 -...

Embodiment 3

[0056] Preparation of 5-(1,2,3-triazole-β-D-glucoside) epigallocatechin gallate (Compd.3) (steps 1, 2 and steps 4, 5, 6, and 7 ):

[0057] the fourth step: Preparation of azide-2,3,4,6-peracetyl-β-glucose:

[0058] The bromo 2,3,4,6-acetyl-β-glucose (1.3g, 3.85mmol) obtained by evaporating to dryness was dissolved in 5mL DMF, and sodium azide (500mg, 7.69mmol) was slowly added under ice-bath conditions, The reaction was terminated after 12 h at room temperature. After the reaction was completed, 10 mL of water was added to quench the reaction, and then the organic phase was extracted with chloroform (3×10 mL). After the organic phase was combined, dried with anhydrous sodium sulfate, concentrated under reduced pressure to obtain a crude product, which was purified by silica gel chromatography (elution Condition: petroleum ether / ethyl acetate=2:1). The product azide-2,3,4,6-acetyl-β-glucose 679.5 mg was obtained, and the yield was 52%. 1 H-NMR (CDCl 3 ,500MHz)δ5.20(t,1H,...

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PUM

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Abstract

According to the formula (I), a epigallocatechin gallate glycoside derivative and a pharmaceutically acceptable salt thereof, a preparation method thereof, a pharmaceutical composition containing thesame as an active ingredient, and an anti-cancer composition in combination with an anti-cancer drug are provided. Compared with the anti-cancer drug alone, the combination of the EGCG derivative andthe anti-cancer drug has better tumor inhibiting effect. The invention further discloses the application of the compounds in preparing the anti-tumor pharmaceutical composition and the preparation.

Description

technical field [0001] The invention belongs to the field of pharmacy, in particular to the field of anticancer drugs. Relating to epigallocatechin gallate (EGCG) glycoside derivatives and pharmaceutical compositions using them as active ingredients, a preparation method thereof, and an anticancer composition prepared from EGCG glycosides and one or more anticancer drugs , and the use of the compound or the anticancer composition in the preparation of an anticancer preparation. Background technique [0002] In recent years, the threat of cancer to human beings has become increasingly prominent, and it has become the first cause of death among urban and rural residents in my country. The top five common cancer mortality rates in cities in China are lung, liver, stomach, esophagus and large intestine. Among them, the still high mortality rate of lung cancer has also evolved into the main factor of human death due to cancer (Jemal, A. et al. CA Cancer JClin. 2011, 2, 69–90.)....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/26C07H19/056C07H1/00A61K31/7048A61K31/7056A61K33/24A61P35/00
CPCC07H15/26A61K31/7048A61K31/7056A61K33/24C07H1/00C07H19/056A61K2300/00
Inventor 盛军王宣军字成庭王晶向泽敏黄业伟王娅吴晓云方崇业刘佳张冬英汪琦唐晗张帮磊王玉娜
Owner YUNNAN AGRICULTURAL UNIVERSITY
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