20(R)-ginsenoside Rg3 derivatives, and preparation method and application thereof

A technology of ginsenosides and derivatives, applied in chemical instruments and methods, drug combinations, glycoside steroids, etc., can solve the problems of unproven tumor inhibitory effect, no synergistic effect, and equivalent inhibitory effect, and achieve the extension zone The effect of improving tumor survival time, improving life extension rate, and increasing tumor suppression rate

Inactive Publication Date: 2016-07-20
富力
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, international application WO9731933A discloses a method for extracting 20(S)-ginsenoside Rg3 derivatives from red ginseng, but due to rough results, it has not been proved whether it has an inhibitory effect on tumors
Although Wang Hui et al. (Food Science, 34(5):45) synthesized 20(S)-ginsenoside Rg3 derivatives in 2013, the inhibitory ability of the derivatives to tumor cells in vitro is not related to the effect of the corresponding amount of ginsenoside Rg3. quite or even slightly worse
[0008] In addition, in an invention patent about 20(S)-ginsenoside Rg3 in the treatment of non-small cell lung cancer, it was found that this component was combined with the chemotherapy drug cyclophosphamide, and no obvious synergistic effect was found (Chinese patent CN101732332A)

Method used

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  • 20(R)-ginsenoside Rg3 derivatives, and preparation method and application thereof
  • 20(R)-ginsenoside Rg3 derivatives, and preparation method and application thereof
  • 20(R)-ginsenoside Rg3 derivatives, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] 1. Add 20(R)-ginsenoside Rg3 (4g, 5.09mmol) into 180ml of dry anhydrous pyridine, stir and dissolve to prepare 20(R)-ginsenoside Rg3 solution;

[0066] In addition to anhydrous pyridine, the organic solvent for dissolving 20(R)-ginsenoside Rg3 in the embodiment of the present invention can also be anhydrous 2,4,6-collidine or anhydrous 2,6-dimethyl pyridine.

[0067] 2. Under the condition of ice bath (0°C), feed nitrogen into the reaction vessel, remove the air, prevent the moisture in the air from contacting the acid chloride reagent, and cause the denaturation of the acid chloride, to 20(R)-ginsenoside Rg3 Add palmitoyl chloride (3.07ml, about 10mmol) dropwise in the solution, stir while adding dropwise, the rate of addition is 1 drop (about 50ul / drop) / 2s (promptly add to 20(R)-ginseng at a rate of one drop per 2 seconds Saponin Rg3 solution is added dropwise with palmitoyl chloride), until the dropwise addition of palmitoyl chloride is completed to obtain a ginseno...

Embodiment 2

[0095] 1. Add 20(R)-ginsenoside Rg3 (4g, 5.09mmol) into 180ml of dry anhydrous pyridine, stir and dissolve to prepare 20(R)-ginsenoside Rg3 solution;

[0096] 2. Under the condition of ice bath (-10°C), feed nitrogen into the reaction vessel to remove the air, prevent the moisture in the air from contacting with the acid chloride reagent, and under the condition of denaturation of the acid chloride, add 20(R)-ginsenoside Rg3 Add palmitoyl chloride (3.07ml, about 10mmol) dropwise in the solution, stir while adding dropwise, the rate of addition is 1 drop / 2s, until the palmitoyl chloride is added dropwise, the ginsenoside-acyl chloride mixture is obtained; wherein, 20(R)- The molar ratio of ginsenoside Rg3 to palmitoyl chloride is 1:1.9.

[0097] In the embodiment of the present invention, the dropping rate in the process of dropping the acylating reagent acid chloride is described by taking 1 drop / 2s as an example, and other dropping rates such as 1 drop / 1-5s are applicable to ...

Embodiment 3

[0103] 1. Add 20(R)-ginsenoside Rg3 (4g, 5.09mmol) into 180ml of dry anhydrous pyridine, stir and dissolve to prepare 20(R)-ginsenoside Rg3 solution;

[0104] 2. Under the condition of ice bath (0°C), feed nitrogen into the reaction vessel, remove the air, prevent the moisture in the air from contacting the acid chloride reagent, and cause the denaturation of the acid chloride, to 20(R)-ginsenoside Rg3 Add palmitoyl chloride (3.07ml, about 10mmol) dropwise in the solution, stir while adding dropwise, the rate of addition is 1 drop / 2s, until the palmitoyl chloride is added dropwise, the ginsenoside-acyl chloride mixture is obtained; wherein, 20(R)- The molar ratio of ginsenoside Rg3 to stearyl chloride is 1:2.3;

[0105] 3. Under the condition of feeding inert gas (nitrogen) into the reaction vessel all the time, after adding the acid chloride reagent dropwise, heat it under stirring to raise the temperature of the ginsenoside-acyl chloride mixture to 5°C, and keep the temperat...

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Abstract

The invention provides 20(R)-ginsenoside Rg3 derivatives represented by formula (I), and a preparation method and an antitumor application thereof. In the formula (I), R1 is H and R2 is CnH2n+1CO, or R1 is CnH2n+1CO and R2 is H, or R1 = R2 = CnH2n+1CO, and n is 3-30.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, specifically, the invention relates to a 20(R)-ginsenoside Rg3 derivative and a preparation method thereof, and also relates to its application in medicine. Background technique [0002] 20(R)-ginsenoside Rg3, whose structure is shown in the following formula, was first isolated and identified by Japanese scholar Kitagawa Isao in 1980. Because the extraction rate is low, the extraction rate extracted from red ginseng (cultivated ginseng is dried or dried and steamed) is only 0.003%, so the price is expensive. [0003] [0004] Later, 20(R)-ginsenoside Rg3 was proved to be one of the active ingredients in ginseng, which can improve and prevent many diseases. For common diseases of middle-aged and elderly people, such as cardiovascular and cerebrovascular diseases, coronary heart disease, weakness of limbs, legs and feet Inconvenience, memory loss are curative. [0005] In recent years, stud...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J17/00A61K31/704A61P35/00
CPCA61P35/00C07J17/005
Inventor 樊宏宇富力王硕柳洋
Owner 富力
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