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Ursolic acid derivative chemically modified by polyethylene glycol and preparation method of ursolic acid derivative

A polyethylene glycol, chemical modification technology, applied in organic chemistry, steroids, medical preparations containing active ingredients, etc., can solve the problem of reducing the anti-tumor activity of derivatives

Inactive Publication Date: 2012-01-25
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has been reported in the literature that the 3-hydroxyl of ursolic acid is very important for the anticancer effect of ursolic acid, and modification of the 3-hydroxyl may reduce the antitumor activity of the resulting derivatives

Method used

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  • Ursolic acid derivative chemically modified by polyethylene glycol and preparation method of ursolic acid derivative
  • Ursolic acid derivative chemically modified by polyethylene glycol and preparation method of ursolic acid derivative
  • Ursolic acid derivative chemically modified by polyethylene glycol and preparation method of ursolic acid derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] compound 2 Preparation of:

[0042] 10 g of ursolic acid was dissolved in 45 mL of pyridine, and 25 mL of acetic anhydride was slowly added dropwise in an ice bath, and the reaction was carried out at room temperature for 8 h after dropping. Stop the reaction, evaporate pyridine under reduced pressure, dissolve the residue with dichloromethane, wash the organic phase with hydrochloric acid (5%), distilled water, and saturated sodium chloride solution successively, and filter the organic phase with anhydrous sodium sulfate to remove water for 2 h. The filtrate was concentrated under reduced pressure at 45°C and then dried to constant weight. The obtained crude product was 10.50 g. The crude product was recrystallized from absolute ethanol to obtain 8.59 g of white needle-like crystals. The crystallization yield was 83.3%, and the total yield was 80.5%. mp: 282~283°C.

[0043] 1 H NMR (600MHz, CDCl 3 ): 5.32(t, 1H, J =3.6 Hz, H-12), 4.42 (t, 1H, J =5.6 Hz, H-3), 2...

Embodiment 2

[0098] a: Dissolve 8 g of ursolic acid in 50 mL of pyridine, slowly add 20 mL of acetic anhydride dropwise in ice bath, and react at room temperature for 9 h after dropping; stop the reaction, evaporate pyridine under reduced pressure, and dissolve the residue in dichloromethane , and successively wash the organic phase with 5% hydrochloric acid, distilled water, and saturated sodium chloride solution, and then filter the organic phase with anhydrous sodium sulfate for 1 h. The filtrate is concentrated under reduced pressure at 50°C and dried to constant Weight, the crude product was obtained, and the crude product was recrystallized with absolute ethanol to obtain compound 2;

[0099] b: 4 g of compound 2 was completely dissolved in 50 mL of dichloromethane, and 4 mL of oxalyl chloride was slowly added dropwise in an ice bath. After the dropwise addition, continued to stir in an ice bath for 0.5 h, and then continued to react at room temperature for 12 h; After the reaction w...

Embodiment 3

[0107] a: Dissolve 12 g of ursolic acid in 40 mL of pyridine, slowly add 30 mL of acetic anhydride dropwise in an ice bath, and react at room temperature for 6 h after dropping; stop the reaction, evaporate pyridine under reduced pressure, and dissolve the residue in dichloromethane , and successively washed the organic phase with 5% hydrochloric acid, distilled water, and saturated sodium chloride solution, and then filtered the organic phase with anhydrous sodium sulfate for 3 h. The filtrate was concentrated under reduced pressure at 40°C and dried to constant Weight, the crude product was obtained, and the crude product was recrystallized with absolute ethanol to obtain compound 2;

[0108] b: 6 g of compound 2 was completely dissolved in 30 mL of dichloromethane, and 7 mL of oxalyl chloride was slowly added dropwise under ice bath conditions. After the dropwise addition, continued to stir in the ice bath for 2 h, and then continued to react at room temperature for 36 h; A...

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Abstract

The invention relates to an ursolic acid derivative chemically modified by polyethylene glycol and a preparation method of the ursolic acid derivative. In the method, a novel ursolic acid derivative with anticancer activity is developed by modifying 28 bits of carboxyl of ursolic acid with butanedioic anhydride, ethylene diamine and polyethylene glycol. As proved by a pharmacological test, the ursolic acid derivative has remarkable in-vitro suppressing capabilities on human liver cancer HepG2 cells, human stomach cancer AGS cells, human stomach cancer BGC-823 cells and human prostatic csarcinoma PC-3 cells.

Description

technical field [0001] The invention specifically relates to a ursolic acid derivative chemically modified by polyethylene glycol and a preparation method thereof. Background technique [0002] Ursolic acid (Ursolic acid, UA), also known as ursolic acid, ursolic acid, belongs to pentacyclic triterpenoids, chemical name (3β)-3-Hydroxyurs-12-en-28-oic acid, molecular formula C 30 h 48 o 3 . It is widely distributed in nature and exists in free form or combined with sugar to form glycosides in various plants. Pharmacological studies have found that ursolic acid has a wide range of biological effects. In addition to protecting the liver, anti-inflammatory, anti-virus, anti-bacterial, and regulating the central nervous system, it also has significant anti-cancer effects, and has few side effects and low toxicity. great potential for clinical application. [0003] The chemical structural formula of ursolic acid: [0004] [0005] At present, domestic research reports on u...

Claims

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Application Information

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IPC IPC(8): C07J63/00C08G65/48A61K31/56A61K31/785A61P35/00
Inventor 白锴凯郭养浩郑允权石贤爱
Owner FUZHOU UNIV
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