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

✍ Scribed by Richard K. Haynes; Hendry Hung-On Pai; Arnd Voerste

• Book ID: 104261613
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 332 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00830-8

✦ Synopsis

In CH& in the presence. of bcnzylamine, artemisinin transfers an oxyg~l atom from the intermediate open hydropcroxide to tertiary amines to form N-ox&s and N-beuzyl-1 1 -azadesoxyartemisinin Basecatalyzed side reactions interfere with the correspondin reaction involving clibydroartemisinin. The reactions serve as a model for biological activity in which the act of bincl@ to a protein liberates hydroperoxide.