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Ursolic acid derivative and preparation method thereof

A technology of ursolic acid and derivatives, applied in the field of ursolic acid derivatives, can solve the problems of not meeting people's requirements or desires for drug effects, not being high enough, and reducing the increase range, etc.

Inactive Publication Date: 2014-01-15
ARMY MEDICAL UNIV
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  • Abstract
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Problems solved by technology

[0009] As can be seen from the above table, with the increase of concentration, the inhibitory rate of this prior art obviously reduces with respect to the increase range of ursolic acid; Satisfy people's requirements or desires for drug effects
In short, in terms of inhibiting the proliferation of human leukemia U937 cells, the inhibition rate of this prior art with the increase of its concentration and the inhibition rate under different concentration conditions are still not high enough

Method used

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  • Ursolic acid derivative and preparation method thereof
  • Ursolic acid derivative and preparation method thereof
  • Ursolic acid derivative and preparation method thereof

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Embodiment Construction

[0029] One, a kind of ursolic acid derivative, the parent in its structure is ursolic acid, and is 28-acyl (8 '-amino caprylic acid) at 28-position, in the present invention, in the 3- of ursolic acid parent The position is hydroxyl; the ursolic acid derivative is arbutane-12-en-28-acyl (8'-aminocaprylic acid), and its structural formula is:

[0030]

[0031] Two, a kind of preparation method of ursolic acid derivative, what this method prepared is the ursolic acid derivative described in this specific embodiment one; The method has following preparation steps:

[0032] (1) Reaction of ursolic acid and acetic anhydride to acetylate and protect the 3-hydroxyl of ursolic acid to generate 3-O-acetyl ursolic acid;

[0033] (2) React 3-O-acetylursolic acid with oxalyl chloride to modify the 28-position to generate 3-O-acetylurbutane-28-acyl chloride intermediate;

[0034] (3) using 3-O-acetylarbutane-28-acyl chloride intermediate as one of the reactants to generate the ursolic ...

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Abstract

The invention provides an ursolic acid derivative and a preparation method thereof. The ursolic acid derivative is bearberry alkane-12-alkene-28-acyl (8'-aminocaprylicacid). The preparation method of the ursolic acid derivative comprises the following steps: firstly, ursolic acid is converted into a crude product of a 3-O-acetyl bearberry alkane-28-acyl chloride intermediate through two steps, then the crude product is used as one of reactants to react with 8-aminocaprylicacid, and finally the crude product and a sodium hydroxide solution are subjected to hydrolysis reaction, so that the ursolic acid derivative is obtained. Compared with the ursolic acid derivative in the prior art, the ursolic acid derivative provided by the invention has more obvious and better effects on the aspect of inhibiting human body leukemia U937 cell proliferation; the preparation method has few steps, the purification method is simple, the cost can be reduced, and the product purity is high.

Description

technical field [0001] The invention relates to a derivative of ursolic acid and a preparation method of the derivative of ursolic acid. Background technique [0002] Ursolic acid (UA), also known as ursolic acid, belongs to pentacyclic triterpenoids, which widely exists in natural plants. Its structural formula is: [0003] [0004] Ursolic acid has a variety of biological activities and has high medicinal value, and its anti-tumor effect is one of its medicinal values. Like many natural extracts, if you want the anti-tumor effect of ursolic acid to play better, you need to use different chemical modification methods to modify the structure of ursolic acid for different tumors. For example, in order to focus on improving the inhibitory effect on the proliferation of human leukemia U937 cells, the application publication number is CN102558282A, and the title is also called "A kind of ursolic acid derivative and its preparation method". and 28-positions were modified. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00
Inventor 张定林高宁刘毅敏李国兵赵先英季卫刚
Owner ARMY MEDICAL UNIV
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