New Route to Antimalarial Artemisinin

  • ChemPubSoc Europe Logo
  • Author: Evenda Dench
  • Published Date: 16 April 2013
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: New Route to Antimalarial Artemisinin

Related Societies

Qinghaosu, or artemisinin, is the most effective antimalarial drug available today because it is fast acting and the malaria parasite has not yet developed resistance to it. However, the total synthesis of qinghaosu is particularly difficult. The most prominent feature of the compound, and the most difficult to incorporate, is the 1,2,4-trioxane and peroxy bridge that is responsible for its antimalarial activity.


Yikang Wu and colleagues at the Shanghai Institution of Organic Chemistry, China, the Swiss Tropical and Public Health Institute, Basel, and the University of Basel, Switzerland, have developed a new synthetic route to qinghaosu and analogues that show good antimalarial activity.

With the aid of a molybdenum catalyst, the stereoselective perhydrolysis of a sterically hindered epoxide ring was achieved at ambient temperature in ethereal H2O2. The resulting hydroperoxide was readily converted into a 1,2,4-trioxane, from which qinghaosu and analogues were constructed. By varying the relative configuration and functionality of the peroxy substrate, some insight into the stereochemical requirements of the key perhydrolysis reaction was also gained.


Some of the new trioxane compounds showed ng mL–1 level in vitro activity against the Plasmodium falciparum parasite that is comparable to, or better than, that of the existing antimalarial drugs chloroquine and artesunate. These potent new analogues and their activity data provide valuable information about structure–activity relationships for the trioxane-type antimalarials and may serve as useful lead compounds.


Article Views: 2379

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH