Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing artemisinin through arteannuic acid

A technology of artemisinic acid and artemisinin, applied in the field of biomedicine, can solve the problems of unfavorable environmental protection and industrial production, cumbersome operation, poor product selectivity, etc., and achieve easy large-scale production, good stereoselectivity, and high product purity Effect

Active Publication Date: 2012-10-10
SHANGHAI JIAO TONG UNIV
View PDF4 Cites 19 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the selectivity of the product obtained is poor, and there are many by-products, resulting in a low total yield of artemisinin (<20%), and it is difficult to realize industrial production
[0005] In summary, the existing methods for the preparation of artemisinin have long synthetic routes, cumbersome operations, poor atom economy, and low overall yield, which are not conducive to environmental protection and industrial production.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing artemisinin through arteannuic acid
  • Method for preparing artemisinin through arteannuic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] (1) Synthesis of dihydroartemisinic acid 2

[0043] Artemisinic acid (100 g, 427 mmol) and 10% Pd / C (4.3 mmol) were added to 1000 mL of methanol, and reacted at -50 °C in a hydrogen atmosphere (1 bar) for 24 hours. The reaction mixture was filtered through celite, and the organic solvent was removed by rotary evaporation to obtain a white solid (99 g, 98%).

[0044] (2) Synthesis of dihydroartemisinic acid 3 peroxide

[0045] Dihydroartemisinic acid (99 g, 420 mmol), potassium dichromate (4.2 mmol), potassium carbonate (4.2 mmol) were added to 1000 mL of acetonitrile. At -78°C, slowly add 30% hydrogen peroxide (420 mmol) dropwise to the system, and react overnight. The organic solvent was removed by rotary evaporation, the residual phase was extracted with ethyl acetate (500mL×3), the combined organic phases were dried over anhydrous sodium sulfate, filtered by suction, the solvent was removed by rotary evaporation, and the product was directly put into the next react...

Embodiment 2

[0049] (1) Synthesis of dihydroartemisinic acid 2

[0050] Artemisinic acid (100 g, 427 mmol) and 10% Pd / C (427 mmol) were added to 1000 mL of isopropanol, and reacted at 25 °C in a hydrogen atmosphere (1 bar) for 12 hours. The reaction mixture was filtered through celite, and the organic solvent was removed by rotary evaporation to obtain a white solid (100 g, 99%).

[0051] (2) Synthesis of dihydroartemisinic acid 3 peroxide

[0052] Dihydroartemisinic acid (100 g, 424 mmol), sodium perchlorate (424 mmol), and pyridine (424 mmol) were added to 1000 mL of acetone. At -78°C, 30% hydrogen peroxide (4.2 mol) was slowly added dropwise to the reaction mixture and reacted overnight. The organic solvent was removed by rotary evaporation, the residual phase was extracted with ethyl acetate (500mL×3), the combined organic phases were dried over anhydrous sodium sulfate, filtered by suction, the solvent was removed by rotary evaporation, and the product was directly put into the next...

Embodiment 3

[0056] (1) Synthesis of dihydroartemisinic acid 2

[0057] Artemisinic acid (100g, 427mmol), Al 2 o 3 / Rh (4.3mmol) was added into 1000mL of methanol, and reacted at -50°C in a hydrogen atmosphere (1 bar) for 24 hours. The reaction mixture was filtered through celite, and the organic solvent was removed by rotary evaporation to obtain a white solid (99 g, 98%).

[0058] (2) Synthesis of dihydroartemisinic acid 3 peroxide

[0059] Dihydroartemisinic acid (99 g, 420 mmol), sodium hypochlorite (4.2 mmol), sodium hydroxide (4.2 mmol) were added to 1000 mL of acetonitrile. At -40°C, 30% hydrogen peroxide (420 mmol) was slowly added dropwise to the system, and reacted overnight. The organic solvent was removed by rotary evaporation, the residual phase was extracted with ethyl acetate (500mL×3), the combined organic phases were dried over anhydrous sodium sulfate, filtered by suction, the solvent was removed by rotary evaporation, and the product was directly put into the next re...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for preparing artemisinin through arteannuic acid. The method comprises the steps that first the arteannuic acid is processed to obtain a dihydroartemisinic acid under the effect of a reducing agent such as sodium borohydride / nickel chloride or a hydrogen / metal catalyst, and then the dihydroartemisinic acid is oxidized into a peroxided dihydroartemisinic acid through peroxide in the presence of the catalyst, and finally the target product artemisinin can be obtained with high yield under the catalyzing of the acid and the effect of oxygen; or a dihydroartemisinic acid derivative can be obtained from the dihydroartemisinic acid based on the protection on carboxyl, and the dihydroartemisinic acid derivative is oxidized into a relevant peroxided dihydroartemisinic acid derivative through the peroxide in the presence of the catalyst, and then the target product artemisinin can be obtained with high yield under the catalyzing of the acid and the effect of the oxygen. Compared with the prior art, the method for preparing the artemisinin through the arteannuic acid has the advantages as follows: the used agent has low cost, and is easy to obtain; the synthetic route is short; the reaction selectivity is high; the preparation process is environmental-friendly; the operation and post-processing are simple; the total yield is high; and the method for preparing artemisinin through the arteannuic acid is applied to industrial production.

Description

technical field [0001] The invention relates to the field of biomedicine, in particular to a method for preparing an antimalarial drug artemisinin. Background technique [0002] Artemisinin, a sesquiterpene lactone antimalarial drug with peroxy groups extracted from the traditional Chinese medicine Artemisia annua, is the first internationally recognized natural medicine discovered in China. The antimalarial mechanism of artemisinin is different from other antimalarial drugs. Its main function is to interfere with the membrane-mitochondrion function of Plasmodium, rather than interfere with folic acid metabolism, resulting in the complete collapse of parasite structure. In addition, artemisinin can be used as raw material to synthesize a variety of its derivatives, such as dihydroartemisinin, artemether, artesunate and so on. These artemisinin drugs have low toxicity and strong anti-masochistic properties, and have been approved by the WTO as the first-choice drugs for the ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/20
CPCC07D493/18
Inventor 张万斌刘德龙袁乾家
Owner SHANGHAI JIAO TONG UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com