Unlock instant, AI-driven research and patent intelligence for your innovation.

Oleanolic acid derivative as well as preparation method and application thereof

A technology of oleanolic acid and acetyloleanolic acid, applied in the directions of drug combination, pharmaceutical formulation, steroid, etc., can solve the problem that the anticancer activity is not significantly improved, the half-lethal concentration of cancer cells is low, and the damage is completely eliminated. The original structure of leanolic acid and other problems can inhibit the growth of tumor cell lines, improve anti-tumor activity, and be suitable for large-scale production.

Active Publication Date: 2014-06-18
ZHEJIANG UNIV
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The existing artificially synthesized oleanolic acid derivatives have complex structures and cumbersome reaction processes. Among them, some oleanolic acid derivatives have destroyed the original structure of oleanolic acid, and these derivatives have great anticancer activity. did not improve significantly
Compared with artificially synthesized oleanolic acid derivatives, natural oleanolic acid derivatives have better anticancer activity, and the semi-lethal concentration of cancer cells is low, but such derivatives have complex structures and are difficult to synthesize artificially. Plant extraction is complex and difficult to achieve mass production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Oleanolic acid derivative as well as preparation method and application thereof
  • Oleanolic acid derivative as well as preparation method and application thereof
  • Oleanolic acid derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1 (the synthesis of oleanolic acid and diethylenetriamine reaction product OA-DETA that 3 hydroxyls are protected with acetyl group)

[0054] (1) Synthesis of oleanolic acid (3-O-acetyl oleanolic acid) protected by acetyl group at the 3-hydroxyl group:

[0055] Oleanolic acid (Mn=456.7, 4.57g) was dissolved in 19 mL of dry pyridine (pridine), and 9.45 mL of acetic anhydride was slowly added dropwise in an ice bath (0° C. ice bath) for a time of After 15 minutes, the ice bath was removed after the dropwise addition was completed, and the reaction was carried out at a room temperature of 25° C. for 5 hours. After the reaction was completed, the precipitate was filtered off, and the obtained filtrate was concentrated. Precipitate three times with water. Precipitate twice with methanol then, obtain white solid (4.061g, productive rate 81.4%), the proton nuclear magnetic resonance spectrum figure of the white solid that obtains is as follows figure 1 As shown,...

Embodiment 2

[0063] Embodiment 2 (the synthesis of oleanolic acid and ethylenediamine reaction product OA-EDA that 3 hydroxyls are protected with acetyl group)

[0064] (1) Synthesis of oleanolic acid (3-O-acetyl oleanolic acid) protected by acetyl group at the 3-hydroxyl group:

[0065] Step is with the synthetic step of 3-O-acetyl oleanolic acid in step (1) in embodiment 1;

[0066] (2) Synthesis of 3-O-acetyl oleanene-28-acid chloride:

[0067] The step is the same as the synthetic step of 3-O-acetyl oleanene-28-acyl chloride in step (2) in Example 2;

[0068] (3) Synthesis of OA-EDA, the bonded product of oleanolic acid and ethylenediamine, which is protected by an acetyl group at the 3-position hydroxyl group:

[0069] Dissolve the reaction product dissolved in step (2) in 15 mL of dry tetrahydrofuran and slowly add it dropwise into 3 mL of ethylenediamine for 15 minutes, react at room temperature 25°C for 24 hours, concentrate after the reaction, and then precipitate with water Th...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses an oleanolic acid derivative which is obtained by covalent binding of oleanolic acid and at least short-chain amine, wherein the molecular weight of the short-chain amine is 20-200. Further, the carboxyl at the 28th site of oleanolic acid is bounded with amino on short-chain amine through an amide bond. The oleanolic acid derivative can improve antitumor activity, has small toxicity on normal cells and is especially suitable for preparation of an anticancer medicament for treating tumor; and compared with bulk pharmaceutical chemical oleanolic acid, the toxicity of the oleanolic acid derivative on tumor cells is greatly improved. The invention also discloses a preparation method of an oleanolic acid derivative. The method is simple and practicable, mild in reaction condition and less in byproducts.

Description

technical field [0001] The invention relates to the field of oleanolic acid derivatives and their preparation, in particular to an oleanolic acid derivative, its preparation method and its application in the preparation of anticancer drugs for treating tumors. Background technique [0002] Oleanolic acid (OA), synonymous with Angelica acid, English name Oleanic acid, chemical name 3β-hydroxy-olea-12-en-28-oic acid, molecular weight 456.71, CAS number 508-02-1, structural formula as follows : [0003] [0004] Oleanolic acid is a pentacyclic triterpenoid, which is widely distributed in nature. For example, it exists in the free form or in the form of glycosides combined with sugar in plants such as P. It is an ideal drug for treating acute icteric biliary hepatitis and chronic viral hepatitis with low toxicity and few side effects. [0005] Studies have shown that oleanolic acid has different inhibitory effects on various tumor cell lines, but generally the inhibition on...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/56A61P35/00
Inventor 申有青史得发唐建斌隋梅花
Owner ZHEJIANG UNIV