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Ursolic acid derivative and preparation method thereof

A technology of ursolic acid and derivatives, which is applied in the field of ursolic acid derivatives and can solve problems such as insignificant effects

Inactive Publication Date: 2012-07-04
ARMY MEDICAL UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, the structure-activity relationship of the ursolic acid derivative has been determined, but the effect of inhibiting the proliferation of other pathological cells is not significant. The effect is basically the same

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

[0026] One, a kind of ursolic acid derivative, the parent in this derivative structure is ursolic acid, among the present invention, on the 28-position of ursolic acid parent, be connected with 28-acyl (7'-aminoheptanoic acid), The ursolic acid derivative is arbutane-12-ene-28-acyl (7'-aminoheptanoic acid), and its structural formula I is:

[0027] ;

[0028] Alternatively, there is 28-acyl (p-aminomethylbenzoic acid) at the 28-position of the parent ursolic acid, the ursolic acid derivative is ursolic-12-ene-28-yl (p-aminomethylbenzoic acid ), and its structural formula II is:

[0029] .

[0030] 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:

[0031] (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;

[0032] (2) React 3...

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Abstract

The invention discloses an ursolic acid derivative and a preparation method thereof. The ursolic acid derivative is ursolic acid-12-alkene-28-acyl(7'-aminoheptylic acid) or ursolic acid-12-alkene-28-acyl(paraaminomethylbenzoicacid). The preparation method comprises the following steps of: transforming ursolic acid into a crude product of a 3-O-acetyl ursolic acid-28-acyl chloride intermediate in two steps; reacting with 7-amino ethyl heptylate hydrochloride or paraaminomethylbenzoicacid methyl ester hydrochloride by taking the crude product as one of reactants; and hydrolyzing with a sodium hydrate aqueous solution to obtain the ursolic acid derivative. The ursolic acid derivative has a good effect on inhibiting the human leukemias U937 cell proliferation which is not achieved in the prior art; and the preparation method has the advantages of small quantity of synthesis reaction steps, simple purification method, saving in cost and high product purity.

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 a variety of medicinal 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. For example, it can inhibit tumor cell growth, induce tumor cell differentiation, resist tumor angiogenesis and induce tumor cell apoptosis. Obviously, like many natural extracts, in order to make the medicinal value of ursolic acid better and have better inhibitory effects on different tumors, it is still necessary to modify the chemical structure of ursolic acid through different chemical modification methods. Make touch ups. [0005] At present, there are many modifications to the st...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61P35/02
Inventor 张定林刘毅敏高宁李国兵赵先英季卫刚
Owner ARMY MEDICAL UNIV
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