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New compound ramification of garcinia acid

A new technology of gambogic acid and derivatives, applied in the direction of active ingredients of nitro compounds, organic chemistry, etc., can solve problems such as low stability, insolubility, and instability of gambogic acid, and achieve good distribution coefficient and low toxicity Side effects, highly stable effects

Inactive Publication Date: 2005-01-12
HANGZHOU MINSHENG PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Gambogic acid is orange-yellow crystalline powder, which has high solubility in organic solvents such as alcohols and ketones, but it cannot be dissolved in water. Although it can be dissolved in strong alkali (such as sodium hydroxide solution), gambogic acid in alkaline solution Xantholic acid is extremely unstable and easily hydrolyzed. The patent CN1309125A uses compound L-arginine to solve the problem of water solubility, but the stability is not very high
At the same time, although the patent CN1309125A has improved the anticancer efficacy of gambogic acid, it is still slightly inferior to anticancer drugs such as camptothecin

Method used

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  • New compound ramification of garcinia acid
  • New compound ramification of garcinia acid
  • New compound ramification of garcinia acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Example 1 Preparation of gambogic acid ketone carbonyl reduction

[0062]In a 250 ml three-neck flask with stirring, a 0-50°C thermometer and a 25 ml constant pressure dropping funnel, add 6.47 grams of gambogic acid (0.01 mol, 97%), 60 ml of methanol, and 0.42 grams of lithium aluminum hydride (0.011 mol, 98%) was dissolved in a constant-pressure dropping funnel with 10 ml of diethyl ether, the stirring was started, and the lithium aluminum hydride solution was slowly added dropwise while controlling the temperature of the methanol solution at 0-5°C. After the dropwise addition was completed, the stirring reaction was continued for more than 3 hours. Then the reactant was poured into 60 g of ice-water mixture while being stirred with a glass rod, extracted three times with 70 ml of ether (30, 30, 10 ml), and the ether solutions were combined. The ether was washed with water until it was neutral, the aqueous phase was discarded, the organic phase was dried over anhydro...

Embodiment 2

[0067] Embodiment two gambogic acid 20 Preparation of C esters

[0068] In a 250 ml three-neck flask with stirring and a thermometer at 0-50°C, add 6.47 grams of gambogic acid (0.01 moles, 97%), add 70 milliliters of ethanol, and stir and dissolve 2.5 grams of DMAP (0.02 moles) completely. Add a small amount of anhydrous magnesium sulfate and stir for 3 hours, remove magnesium sulfate by filtration, 2.5 grams (0.02 moles) of DMAP and 1.8 grams (0.02 moles) of EDC, stir and react at room temperature for more than 2 hours, and pour the reactant into ice water , extract the target product in the decantate three times (40, 30, 10) with 80 milliliters of ether, discard the water phase, combine the ether phase, remove the organic solvent after drying with anhydrous sodium sulfate, and the crude product obtained is separated with a silica gel column , obtain the higher gambogic acid ester of purity, promptly obtain the R in the general formula (I) 1 for CH 3 CH 2 O- gambogic acid...

Embodiment 3

[0075] Example three gambogic acid 30 Preparation of C amides

[0076] In a 250 ml three-neck flask with stirring and a 0-50° C. thermometer, add 50 ml of acetonitrile and 6.47 g of gambogic acid (0.01 mol, 97%). After stirring to dissolve completely, add a small amount of anhydrous magnesium sulfate and stir for 3 hours, then filter to remove magnesium sulfate. Add 1.45 g (0.02 mol) of butylamine, 2.5 g (0.02 mol) of DMAP and 1.8 g (0.02 mol) of EDC, and stir the reaction at room temperature for more than 6 hours. The reactant was poured into ice water, and the target product in the decantate was extracted three times (40, 30, 10) with 80 ml of ether, the water phase was discarded, the ether phase was combined, and after drying with anhydrous sodium sulfate, the organic solvent was removed. The obtained crude product is separated with a silica gel column to obtain gambogic acid butyramide with higher purity. Promptly obtain the R in the general formula (I) 1 for CH 3 (CH...

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Abstract

This invention relates to modification of three isomers of total garcinolic acid, and shows their general formulas: (I), (II) and (III). This invention also describes the three noval compounds, and their pharmaceutically acceptable salts, and their prepn. methods, where: X1, X2, R1, R2, (R3), (R6), (R7), (R9), (R11), R4, R5, R8, R10, R12 are illustrated as specification of this invention.

Description

technical field [0001] The present invention relates to new compounds for treating cancer and broad-spectrum antibacterial-gambogic acid, neogambogic acid, allogambogic acid series derivatives and a preparation method thereof. Background technique [0002] Garcinia cambogia is a dry resin secreted by the Garcinia cambogia tree. It is cold in nature, sour, pungent, astringent, and poisonous. There are many ointments, pills, and powders with gamboge as the main component in the past. Garcinia is recorded in the United States Pharmacopoeia, and its active ingredient is mainly gambogic acid (including a small amount of neogambogic acid and allogambogic acid). General chemotherapy and anticancer drugs affect the normal hematopoietic system and white blood cells while killing cancer cells. When gambogic acid is used as an anticancer drug, it can selectively kill cancer cells without affecting the normal hematopoietic system and white blood cells. Therefore, total gambogic acid i...

Claims

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Application Information

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IPC IPC(8): A61K31/04C07D493/22
Inventor 王树龙
Owner HANGZHOU MINSHENG PHARM CO LTD
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