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Dihydroartemisinin higher fatty acid ester and preparation method thereof

A technology of dihydroartemisinin and higher fatty acids, applied in organic chemistry, fermentation, antibacterial drugs, etc., can solve the problems of affecting enzyme selectivity and low reaction efficiency, and achieve improved solubility, high yield, and increased The effect of amphiphilicity

Active Publication Date: 2014-01-08
中科蓝海测试(天津)科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the esterification reaction catalyzed by lipase is carried out in a non-aqueous medium, the water in the reaction medium reduces the reaction efficiency and affects the selectivity of the enzyme.

Method used

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  • Dihydroartemisinin higher fatty acid ester and preparation method thereof
  • Dihydroartemisinin higher fatty acid ester and preparation method thereof
  • Dihydroartemisinin higher fatty acid ester and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1 prepares dihydroartemisinin stearate

[0046]

[0047]Dihydroartemisinin and stearic acid were dissolved in tert-butanol at a ratio of 1:6 (molar ratio), and the concentration of dihydroartemisinin in tert-butanol was 1 mg / ml. Add lipase Novozyme 435 at 60°C with a concentration of 4 mg / mL, place it in a shaker and shake at a speed of 60 rpm / min. After reacting for 5 hours, add 100 g of molecular sieve 4A to 1L of the reaction solution. Molecular sieve 4A was activated at 150° C. for 24 hours in advance. Molecular sieve 4A removed the water generated by the esterification reaction. After a total of 96 hours of reaction, the enzyme and molecular sieve were removed by filtration. Concentrate under reduced pressure to remove the solvent to obtain the reaction product substance. The reaction product was separated by column chromatography, and the mobile phase was ethyl acetate:petroleum ether 60-90°C=1:1.5. The yield of dihydroartemisinin stearate (F) obta...

Embodiment 2

[0048] Embodiment 2 prepares dihydroartemisinin laurate

[0049]

[0050] Dihydroartemisinin and lauric acid were dissolved in tert-butanol at a ratio of 1:6 (molar ratio), and the concentration of dihydroartemisinin in tert-butanol was 1 mg / ml. Add lipase Novozyme 435 at 60°C with a concentration of 4 mg / mL, place it in a shaker and shake at a speed of 60 rpm / min. After reacting for 5 hours, add molecular sieve 4A in an amount of 100 g to 1 L of liquid. Molecular sieve 4A is activated at 150°C for 24 hours in advance. Molecular sieve 4A removes the water generated by the esterification reaction. After 96 hours of reaction, the enzyme and molecular sieve are removed by filtration. Concentrate under reduced pressure to remove the solvent to obtain the product substance. The reaction product was separated by column chromatography, and the mobile phase was ethyl acetate:petroleum ether 60-90°C=1:2. The yield of dihydroartemisinin laurate (G) obtained by chromatographic separ...

Embodiment 3 2

[0051] Embodiment 3 The reaction of dihydroartemisinin and lauric acid in different ratios

[0052] Dihydroartemisinin and lauric acid are dissolved in tert-butanol at the ratio of 1:3, 1:4, 1:5, 1:7, 1:8 (molar ratio), dihydroartemisinin in tert-butanol The concentration in is 1mg / ml. At 60°C, lipase Novozyme 435 was added at a concentration of 4 mg / mL, and placed in a shaker to shake and stir. After reacting for 5 hours, add molecular sieve 4A in an amount of 100 g to 1 L of liquid. Molecular sieve 4A is activated at 150°C for 24 hours in advance. Molecular sieve 4A removes the water generated by the esterification reaction. After 96 hours of reaction, the enzyme and molecular sieve are removed by filtration. The solvent was removed by concentration under reduced pressure to obtain the product substance. The reaction product was separated by column chromatography, and the mobile phase was ethyl acetate:petroleum ether 60-90°C=1:2.

[0053] The yield of dihydroartemisinin ...

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Abstract

The invention discloses a dihydroartemisinin higher fatty acid ester and a preparation method thereof. The method adopts lipase as a catalyst, carries out a structure modification on the 10th position carbon of dihydroartemisinin, and then subjecting the hydroxyl group on the 10th carbon of dihydroartemisinin to carry out an esterification reaction with higher fatty acid ester. Specifically, the preparation method takes lipase Novozyme 435 as the catalyst, stearic acid and lauric acid as the acyl group donors, tertiary butanol as the reaction solvent, and 4A molecular sieve as the water absorbing agent during the esterification reaction. The prepared artemisinin esterification product has an oil and water amphiphilicity, and shows a good specificity in the in-vitro antimicrobial tests. The dihydroartemisinin higher fatty acid ester and the preparation method thereof have an important meaning on improving artemisinin solubility in water and oil so as to make artemisinin into a proper dosage form.

Description

technical field [0001] The invention relates to a dihydroartemisinin higher fatty acid ester and a preparation method thereof. Background technique [0002] Artemisinin (artemisinin) is a new type of antimalarial drug extracted from Artemisia annua L., a plant of Compositae. It has the characteristics of high efficiency, quick action and low toxicity. Herbal medicine is also the first traditional Chinese medicine product that is truly recognized worldwide. Artemisinin has the shortcomings of high short-term reflammability, low solubility in oil and water, and difficulty in making suitable dosage forms. Therefore, it has become a research hotspot to modify its structure and find suitable artemisinin derivatives. At present, many derivatives with higher antimalarial activity have been found, and these compounds mainly modify the 10-carbon atom of artemisinin. [0003] [0004] Artemisinin Dihydroartemisinin [0005] 1. Structural modification of artemisinin [0006] Und...

Claims

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Application Information

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IPC IPC(8): C07D493/20A61P31/04
CPCC07D493/20C12P17/181
Inventor 霍清杨晓芳缪刚
Owner 中科蓝海测试(天津)科技有限公司
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