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Preparation method of antitumor active compound

A technology of catalysts and natural products, which is applied in the field of preparation of anti-tumor active compounds, can solve the problems of complex synthesis methods and high commercial prices, and achieve the effects of simple preparation methods, simple separation, and easy control of reaction conditions

Active Publication Date: 2017-09-12
WEIFANG MEDICAL UNIV +3
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Problems solved by technology

Active natural products containing D-glucose fragments are widely distributed in nature. Such compounds are of great significance in biology and pharmacy, but the raw material D-glucose used to synthesize such compounds, the existing synthetic methods are relatively complicated. resulting in higher commercial prices

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  • Preparation method of antitumor active compound
  • Preparation method of antitumor active compound

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Embodiment Construction

[0017] A kind of preparation method of glycoside natural product 1 of the present invention comprises the following steps:

[0018]

[0019] (1) Weigh the hydroxyacetylated glucose intermediate (35g, 89.7mmol) obtained in step (1), triethylamine (4.75g, 46.9mmol), 3,4-dimethoxyphenol (20g, 129.7mmol), were added in dichloromethane (250mL) successively, at 0°C, boron trifluoride ethyl ether silica gel (50g) was added in batches, and then naturally rose to room temperature for 9 hours; then the organic phase was sequentially washed with saturated sodium bicarbonate , washed with saturated brine, filtered, concentrated, and recrystallized with anhydrous methanol to obtain 40.95 g of a glycoside intermediate substituted at the anomeric carbon position of glucose, with a yield of 94.3%.

[0020] (2) Weigh the glycoside intermediate (5.0 g, 10.3 mmol) substituted by the anomeric carbon position of glucose obtained in step (1), dissolve it in dry methanol (140 mL), add 25% of sodi...

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Abstract

The invention relates to a preparation method of antitumor active compound, belonging to the field of medicinal chemistry. The method comprises the steps of enabling commercialized fully-acetylated glucose serving as a starting raw material and methylene dichloride serving as a solvent to react with 3, 4-dimethoxyphenol under the catalytic action of boron trifluoride ether so as to form a glucose anomeric carbon position-substituted glycoside intermediate; then, removing acetyl under the alkaline condition of sodium methylate, and enabling the product to have a regioselective chemical reaction with benzoyl chloride prepared by using full benzyl-protected anhydrous gallic acid so as to obtain a key glycosyl intermediate; finally, carrying out palladium-carbon reduction to remove benzyl protection. The glycoside natural product 1 is formed in high yield by means of simple and efficient reactions in the four steps; the prepared glycoside natural product has good tumor cytotoxic activity. The structural formula of the glycoside natural product 1 is described in the description.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method of an antitumor active compound. Background technique [0002] Sugar compounds, amino acids, terpenes, etc. are natural chiral raw materials for the construction of chiral compounds, and are widely used in the synthesis of many natural active chiral compounds or the preparation of catalysts and chiral auxiliary agents. Active natural products containing D-glucose fragments are widely distributed in nature. Such compounds are of great significance in biology and pharmacy, but the raw material D-glucose used to synthesize such compounds, the existing synthetic methods are relatively complicated. This results in higher commercial prices. Therefore, it is of great application value to study the preparation of a glycoside natural product and its application in active natural products. Contents of the invention [0003] The purpose of the present invention is...

Claims

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Application Information

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IPC IPC(8): C07H15/203C07H1/00C07H1/06A61P35/00
CPCC07H1/00C07H1/06C07H15/203
Inventor 李法辉
Owner WEIFANG MEDICAL UNIV
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