Ring opening of artemisinin (qinghaosu) and dihydroartemisinin and interception of the open hydroperoxides with Formation of N-oxides — a chemical model for antimalarial mode of action

In CH2Cl2 in the presence of benzylamine, artemisinin transfers an oxygen atom from the intermediate open hydroperoxide to tertiary amines to form N-oxides and N-benzyl-11-azadesoxyarte-misinin. Base-catalyzed side reactions interfere with the corresponding reaction involving dihydro-artemisinin. Th...

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Bibliographic Details
Published in:Tetrahedron letters 1999-06, Vol.40 (25), p.4715-4718
Main Authors: Haynes, Richard K., Pai, Hendry Hung-On, Voerste, Arnd
Format: Article
Language:English
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Summary:In CH2Cl2 in the presence of benzylamine, artemisinin transfers an oxygen atom from the intermediate open hydroperoxide to tertiary amines to form N-oxides and N-benzyl-11-azadesoxyarte-misinin. Base-catalyzed side reactions interfere with the corresponding reaction involving dihydro-artemisinin. The reactions serve as a model for biological activity in which the act of binding to a protein liberates hydroperoxide. Artemisinin in the presence of benzylamine transfers an oxygen atom via the open hydroperoxide to tertiary amines to form N-oxides.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)00830-8