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Process for synthesizing parthenolide derivative and uses thereof

A technology of parthenolide and a synthesis method, which can be applied in directions such as drug combinations, nervous system diseases, non-central analgesics, etc., can solve problems such as reducing production costs, and achieve the effects of reducing production costs, high safety, and easy operation.

Inactive Publication Date: 2008-09-24
BEIJING SUNHO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] When the present invention uses sodium ethoxide as a catalyst to modify the parthenolide structure, the yield of the final product is compared with US2005272716A1, and it is found that the yield of the final product is also above 85%, which is the same as that disclosed in the comparative literature. The efficiency is the same, but it solves the problem of industrial practicability, and the reaction conditions can be carried out only under stirring at room temperature, the operation is simple, the requirements for synthesis instruments and site facilities are not high, and it can be carried out under ordinary conditions, which greatly reduces the Cost of production

Method used

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  • Process for synthesizing parthenolide derivative and uses thereof
  • Process for synthesizing parthenolide derivative and uses thereof
  • Process for synthesizing parthenolide derivative and uses thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Preparation of 11,13-dihydro-13-dimethylamino parthenolide

[0030] Add 200mg (0.8mmol) of parthenolide, 180mg (4mmol) of dimethylammonia, and 476mg (7mmol) of sodium ethoxide into 80mL of ethanol, stir at room temperature for 24 hours, make it fully react, evaporate the solvent under reduced pressure, and the residue After silica gel column chromatography, chloroform-methanol 50:1-1:1 gradient elution, TLC or HPLC detection, collect fractions containing 11,13-dihydro-13-dimethylaminoparthenolide, and finally obtain 216 mg of product (yield 92%), compound purity 98.51%. Compound melting point: 142.8-1143.7°C; 1 H-NMR (500MHz, CDCl3): δ5.24(1H, d), 3.82(1H, t), 2.76(2H, m), 2.64(1H, dd), 2.53-2.29(3H, m), 2.27( 6H, s), 2.20-1.95 (5H, m), 1.68 (3H, s), 1.35 (3H, s), 1.30-1.16 (1H, m);

[0031] 13 C-NMR (500MHz, CDCl 3 ): δ175.9, 134.8, 124.2, 82.1, 66.8, 61.9, 58.1, 47.9, 46.5, 46.1, 40.8, 36.2, 30.3, 24.5, 17.8, 16.8; EI-MS: M / Z293 (M + ); UV(MeOH) λmax(logε): 210n...

Embodiment 2

[0033] Preparation of 11,13-dihydro-13-piperidinyl parthenolide

[0034] Add 200mg (0.8mmol) of parthenolide, 272mg (3.2mmol) of piperidine, and 476mg (7mmol) of sodium ethoxide into 80mL of ethanol, stir at room temperature for 24 hours, make it fully react, evaporate the solvent under reduced pressure, and the residue Silica gel column chromatography, chloroform-methanol 50:1-1:1 gradient elution, TLC or HPLC detection, collected fractions containing 11,13-dihydro-13-piperidinyl parthenolide, and finally obtained 233 mg of product (yield 87%), compound purity 99.26%.

Embodiment 3

[0036] Preparation of 11,13-dihydro-13-pyridyl parthenolide

[0037] Add 200mg (0.8mmol) of parthenolide, 0.53mL (4.8mmol) of pyridine, and 476mg (7mmol) of sodium ethoxide into 80mL of ethanol, stir at room temperature for 24 hours, and make it fully react. Silica gel column chromatography, chloroform-methanol 50: 1-1: 1 gradient elution, TLC or HPLC detects, collects the fraction containing 11,13-dihydro-13-pyridyl parthenolide, and finally obtains 213 mg of product ( Yield 81%), compound purity 98.37%.

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Abstract

The present invention relates to a synthetic method of derivatives of parthenolide lactone. Parthenolide lactone and nitrogen-containing compounds are used as the raw materials of the reaction; ethanol sodium is used as a catalyst; the mixture reacts in a certain solvent and at a certain temperature; thus the derivatives of the parthenolide lactone can be prepared. After acidification, the salts of the derivatives can be prepared with greatly improved water solubility. The improved salts of the derivatives of the parthenolide lactone can be used for preparing injection so as to better treat tumors.

Description

technical field [0001] The invention belongs to the field of chemical drug synthesis, and in particular relates to the synthesis of nitrogen-substituted parthenolide derivatives from parthenolide. The polarity of parthenolide after chemical modification is increased, and it is more suitable for making injection preparations. Background technique [0002] Parthenolide is a sesquiterpene lactone compound with an α-methylene-γ-lactone group in its molecule. There are many studies on parthenolide. In Europe and the United States, parthenolide is used to treat migraine and joint pain. Its main component is parthenolide. In recent years, research on parthenolide has found that parthenolide also has anti-tumor activity. , such as inhibiting the growth of colon cancer, prostate cancer, breast cancer, bladder cancer, and leukemia cancer cells. [0003] Parthenolide is a kind of low polar component, which has strong fat solubility and low solubility in water, which greatly limits the...

Claims

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Application Information

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IPC IPC(8): C07D307/77C07D407/06A61K31/365A61K31/4525A61K31/443A61K9/19A61P35/00A61P25/06A61P29/00
Inventor 张树祥熊国裕
Owner BEIJING SUNHO PHARMA
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