A class of indole ursolic acid derivatives, preparation method and use thereof

A technology of indole derivatives and ursolic acid, applied in the field of preparation of indole derivatives of ursolic acid

Active Publication Date: 2016-09-14
麦特绘谱生物科技(上海)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And on this basis, the carboxyl group is esterified and amidated, and the structure of the derivative is relatively novel, which has not been reported at home and abroad.

Method used

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  • A class of indole ursolic acid derivatives, preparation method and use thereof
  • A class of indole ursolic acid derivatives, preparation method and use thereof
  • A class of indole ursolic acid derivatives, preparation method and use thereof

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Experimental program
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Effect test

Embodiment 1

[0022] The synthesis of embodiment 1 oxidized ursolic acid (III)

[0023] Ursolic acid (1g, 2mmol) was dissolved in 150ml of acetone, and the reaction was placed in ice water and stirred for 15min, then slowly added Jones reagent dropwise (26.72g of chromium trioxide was dissolved in 23ml of concentrated sulfuric acid, then diluted to 100ml with water. obtained) 1ml, the reaction was stirred at room temperature for 5h, 45ml of isopropanol was added and stirred for 30min, and the precipitate was filtered off, and the solution was concentrated under reduced pressure to remove the solvent. Recrystallization from methanol gave white crystals of 3-oxyursolic acid III (0.56 g, 64%).

[0024] m.p.276-278°C; 1 H NMR (CDCl 3 ,300MHz):δ0.88(s,3H),0.91(d,J=6.3Hz,3H),0.96(s,3H),0.95(m,2H),0.99(d,J=6.0Hz,3H) ,1.07(s,3H),1.11(s,3H),1.13(s,3H),1.36(m,5H),1.52(m,5H),1.64(td,J=14.3,7.0Hz,1H), 1.76(dd,J=13.6,7.0Hz,1H),1.94(m,2H),2.24(d,J=11.2Hz,1H),5.31(m,1H); IR(KBr,cm -1 ):2930,1718,1657...

Embodiment 2

[0025] Embodiment 2 The synthesis of the phenylhydrazine hydrochloride of p-methyl substituent

[0026] Dissolve p-methylaniline (0.32g, 3mmol) in 3ml of 20% hydrochloric acid, dissolve sodium nitrite (0.28g, 4mmol) in 0.7ml of water, and slowly add it dropwise to the above solution under ice-bath conditions. After stirring and reacting for 1 h under the conditions, the tin protochloride (1.354 g, 6 mmol) solution dissolved in 1.8 ml of 35% hydrochloric acid was slowly dripped into the above reaction for 2 h, and the filtrate was removed by suction filtration to obtain solid phenylhydrazine hydrochloride ( 0.34 g, 70%).

Embodiment 3

[0027] Embodiment 3 The synthesis of the phenylhydrazine hydrochloride of p-methoxy substituent

[0028] P-methoxyaniline (0.37g, 3mmol) was dissolved in 3ml of 20% hydrochloric acid, sodium nitrite (0.28g, 4mmol) was dissolved in 0.7ml of water and slowly added dropwise to the above solution under ice-bath conditions, and the mixture was ice After stirring and reacting for 1 h under bath conditions, slowly drop the tin protochloride (1.354 g, 6 mmol) solution dissolved in 1.8 ml of 35% hydrochloric acid into the above reaction for 2 h, remove the filtrate by suction filtration to obtain solid phenylhydrazine hydrochloride (0.38 g, 69%).

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Abstract

The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a preparation method of a class of indole ursolic acid derivatives having human tumor cytotoxic activity, a pharmaceutical composition containing them and an antitumor application thereof. Pharmacological experiments show that the indole ursolic acid derivatives of the present invention have significant inhibitory effects on two tumor cell strains, such as human liver cancer cells (SMMC-7721, HepG2), and have the value of developing anti-tumor drugs.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a preparation method of a class of indole ursolic acid derivatives having human tumor cytotoxic activity, a pharmaceutical composition containing them and an antitumor application thereof. Background technique [0002] Cancer is one of the major malignant diseases with the highest mortality rate in the world. According to statistics, 1.5 million people die from cancer every year in my country, ranking first in the cause of death. At present, chemotherapy is still one of the basic means of treating tumors. However, the existing chemotherapeutic drugs still have many deficiencies. This is mainly because the vast majority of anti-tumor drugs are anti-cell proliferation agents, such as alkylating agents, DNA-binding agents, etc., and their treatment is based on the fact that tumor cells have a higher proliferation rate, so they do not really selectively act...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00A61K31/58A61P35/00A61P1/16
Inventor 谷文郝云苗婷婷张康平张广王石发
Owner 麦特绘谱生物科技(上海)有限公司
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