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20(S)-ginsenoside Rh2 derivatives for regulating and controlling ER Alpha/ER Beta-TNF Alpha channel as well as preparation and anti-tumor application thereof

A technology of ginsenosides and derivatives, which is applied in the direction of antineoplastic drugs, anti-inflammatory agents, drug combinations, etc., and can solve the problems of poor solubility and low bioavailability of ginseng diol

Inactive Publication Date: 2013-01-09
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But G-Rh2 and protopanaxadiol have poor solubility and low bioavailability

Method used

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  • 20(S)-ginsenoside Rh2 derivatives for regulating and controlling ER Alpha/ER Beta-TNF Alpha channel as well as preparation and anti-tumor application thereof
  • 20(S)-ginsenoside Rh2 derivatives for regulating and controlling ER Alpha/ER Beta-TNF Alpha channel as well as preparation and anti-tumor application thereof
  • 20(S)-ginsenoside Rh2 derivatives for regulating and controlling ER Alpha/ER Beta-TNF Alpha channel as well as preparation and anti-tumor application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Preparation of 20(S)-protopanaxadiol-12β-2'-chloroacetate.

[0071]

[0072] Compound 1

[0073] 100mg (0.0434mmol) of protopanaxadiol was placed in a 25ml dry single-necked flask, and 10ml of anhydrous chloroform was added and stirred until completely dissolved. 70 μl (0.20 mmol) of triethylamine was added to the above solution, and after stirring, 25 μl (0.13 mmol) of chloroacetyl chloride was added, which immediately produced a large amount of white mist. Add 35X10-3ml triethylamine and 15μl chloroacetyl chloride in the middle. The reaction generates a small polar point, and the reaction situation is the same as the first experiment. After reacting at room temperature for 48 hours, the raw materials disappeared. Stop the reaction, add 10ml of water, stir for 10min, add 20ml of chloroform to extract 3 times, combine the chloroform layers, dry over anhydrous sodium sulfate, spin off the solvent under reduced pressure, and separate through the column with dichloromethane:...

Embodiment 2

[0075] Preparation of 20(S)-protopanaxadiol-12β-2`-N,N-dimethyl acetate

[0076]

[0077] Compound 2

[0078] 10 mg (0.0186 mmol) of the product in Example 1 was placed in a 10 ml dry single-necked flask, 2 ml of anhydrous acetonitrile was added, and stirred until completely dissolved. About 7 mg (0.0480 mmol) of anhydrous potassium carbonate was added to the above solution, and after stirring for 5 min, 2 mg (0.025 mmol) of dimethylamine hydrochloride was added. After stirring for 10 min at room temperature, transfer to an oil bath and heat to 50°C. The reaction produces a large polar point, which is visible after iodine smoke. The raw material has no hydrolysis. The raw materials disappeared after about 2.5 days of reaction. Stop the reaction, cool to room temperature, and spin off the solvent under reduced pressure. Add 2ml of water, dissolve the obtained solid, add 5ml of ethyl acetate and extract 3 times, pipette the organic layer, combine the ethyl acetate layer, dry ove...

Embodiment 3

[0080] Preparation of 20(S)-protopanaxadiol-12β-phthalic acid benzoate and its ammonium salt

[0081]

[0082] Compound 3

[0083] 100mg (0.0434mmol) of protopanaxadiol was placed in a 25ml dry single-necked flask, and 10ml of anhydrous chloroform was added and stirred until completely dissolved. Add 360mg (0.20mmol) of 2-sulfobenzoic anhydride to the above solution, react overnight at 50°C under nitrogen protection, then cool to 0°C in an ice-salt bath, add methanol ammonia solution, stir for 2 hours, then distill the solvent Column chromatography was separated to obtain 6 mg of 20(S)-G-Rh2 derivative 20(S)-protopanaxadiol-12β-phthalate. 1H-NMR: δ (ppm, DMSO-d6): 5.15 (t, 1H, H-24), 4.85 (m, 1H, H-12), 7.20-7.8 (m, 4H, H-Ar)

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Abstract

The invention relates to an ER Alpha / ER Beta-TNF Alpha channel which regulates and controls formation, growth and apoptosis processes of tumor cells and can be taken as a signal probe and a new medicine target spot. The invention relates to the preparation and the application of 20(S)-ginsenoside Rh2 derivatives with anti-tumor activity. Medicines containing the 20(S)-ginsenoside Rh2 derivatives and salts thereof, which is provided in the invention, are mainly used for treating tumors and other diseases; and compared with 20(S)-ginsenoside-Rh2 and 20(S)-protopanoxadiol, the medicines have stronger anti-tumor activity. A structural general formula (I) and a structural general formula (II) are as shown in the specification.

Description

Technical field: [0001] The present invention relates to 20(S)-ginsenoside Rh2 derivatives. [0002] The invention also relates to a preparation method of the derivative; [0003] The invention also relates to its application in the preparation of anti-tumor drugs. Background technique: [0004] The root of the medicinal plant Panax ginseng CAMeyer is a traditional precious Chinese medicinal material. Its main medicinal active ingredient-ginsenoside (G) is a tetracyclic triterpene dammarane composed of isoprene units (five carbons). Molecular compound, composed of ginsengdiol and ginsenosides. At present, ginsengdiol saponins mainly include G-Rb1, G-Rb2, G-Rc, G-Rd, G-Rg3, G-Rh2 and G-Rh3. Ginseng triol-type saponins mainly include G-Re, G-Rf, G-Rg1, G-Rg2, G-Rh1. Among them, the ginsenosides Rh2, Rg3, Compound K, 20(S)-protopanaxadiol type and 20(R)-protopanaxadiol, which belong to the ginsengdiol group, have been proved by in vivo and in vitro experiments to have very significa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J17/00A61K31/704A61P35/00A61P19/02A61P29/00A61P25/28
Inventor 罗志勇刘苏友黄景嘉张建亭
Owner CENT SOUTH UNIV
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