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Ursolic acid derivatives with anticancer activity and preparation method thereof

An anticancer activity, ursolic acid technology, applied in antitumor drugs, drug combinations, steroids and other directions, can solve the problems that have not yet been involved in the connection between natural α-amino acids and ursolic acid, and achieve the product with significant pharmacological activity and preparation. simple steps

Inactive Publication Date: 2011-11-30
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, when amino acid modified ursolic acid is used in existing patents or documents, the C-28 carboxyl group of ursolic acid and the α-amino group of natural α-amino acid are all used to form an amide bond to prepare amino acid modified ursolic acid. Fruit acid derivatives, which have not been involved in the research of linking natural α-amino acids with ursolic acid in other ways

Method used

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  • Ursolic acid derivatives with anticancer activity and preparation method thereof
  • Ursolic acid derivatives with anticancer activity and preparation method thereof
  • Ursolic acid derivatives with anticancer activity and preparation method thereof

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Experimental program
Comparison scheme
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Embodiment 1

[0039] compound 2 Preparation of:

[0040]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, and wash the organic phase with hydrochloric acid (5%), distilled water, and saturated sodium chloride solution successively, and filter the organic phase after dehydrating with anhydrous sodium sulfate for 2 h , the filtrate was concentrated under reduced pressure at 45°C and then dried to constant weight, and 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.

[0041] 1 H NMR (600MHz, CDCl 3 ): 5.32 (t, 1H, J =3.6 Hz, H-12), 4.42 (t, 1H, J =5.6 ...

Embodiment 2

[0076] The concrete preparation method of this ursolic acid derivative is:

[0077] a: Dissolve 5 g of ursolic acid in 40 mL of pyridine, slowly add 20 mL of acetic anhydride dropwise under ice bath conditions, and react at room temperature for 6 h after the addition; stop the reaction, evaporate pyridine under reduced pressure, and wash the residue with dichloromethane Dissolve, and wash the organic phase with 5% hydrochloric acid, distilled water, and saturated sodium chloride solution successively, and then filter the organic phase with anhydrous sodium sulfate for 1 h, then concentrate the filtrate under reduced pressure at 40 °C and dry it to Constant weight, drying temperature is 60°C, compound 2 is obtained;

[0078] b: 4 g of compound 2 was completely dissolved in 30 mL of dichloromethane, and 5 mL of oxalyl chloride was slowly added dropwise under ice-bath conditions. After the dropwise addition, continued to stir in the ice bath for 0.5 h, and then continued to react...

Embodiment 3

[0085] The concrete preparation method of this ursolic acid derivative is:

[0086] a: Dissolve 15 g of ursolic acid in 50 mL of pyridine, slowly add 30 mL of acetic anhydride dropwise under ice bath conditions, and react at room temperature for 9 h after the addition; stop the reaction, evaporate pyridine under reduced pressure, and wash the residue with dichloromethane dissolved, and the organic phase was washed with 5% hydrochloric acid, distilled water, and saturated sodium chloride solution in sequence, and the organic phase was dehydrated with anhydrous sodium sulfate for 3 h, then filtered, and the filtrate was concentrated under reduced pressure at 50°C and dried to Constant weight, drying temperature is 70 ° C, to obtain compound 2;

[0087] b: 6 g of compound 2 was completely dissolved in 50 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, an...

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Abstract

The invention relates to ursolic acid derivatives with anticancer activity and a preparation method thereof. In the method, a carbonoxyl group at the C-28 position of ursolic acid is connected with natural alpha-amino acid through ethanediamine in a mode of forming an amido bond to synthesize a series of ursolic acid derivatives with anticancer activity. In-vitro pharmacological experiments indicate that the ursolic acid derivatives chemically modified by amino acid have obvious in-vitro inhibition effect on human liver cancer HepG2 cells, human colon cancer HT-29 cells, human gastric cancer AGS and BGC-823cells, and human prostatic cancer PC-3 cells.

Description

technical field [0001] The invention specifically relates to an ursolic acid derivative with anticancer activity and a preparation method thereof. Background technique [0002] At present, domestic research reports on ursolic acid mostly focus on the extraction and separation technology and pharmacological research of ursolic acid, especially the research on the anticancer effect of ursolic acid has been reported at home and abroad. For example, "Research progress of ursolic acid antitumor effect and its mechanism" by Wang Tao et al. ("Pharmaceutical Biotechnology", 2008, 15[2]); "Research progress of ursolic acid pharmacology" by Xiong Bin et al. ("Foreign Medicine "Pharmaceutical Volume", 2004, 31[[3]); Xia Guohao et al. "Research Progress on the Antitumor Effect of Ursolic Acid" ("Foreign Medical Oncology Volume", 2002, 29[6]); and so on. Studies have shown that ursolic acid has anti-initiative mutation, anti-cancer effect, anti-oxidation, cytotoxicity, induction of canc...

Claims

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Application Information

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