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

Authors
Haynes, RK Pai, HHO Voerste, A
Citation
Rk. Haynes et al., 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, TETRAHEDR L, 40(25), 1999, pp. 4715-4718
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
25
Year of publication
1999
Pages
4715 - 4718
Database
ISI
SICI code
0040-4039(19990618)40:25<4715:ROOA(A>2.0.ZU;2-H
Abstract
In CH2Cl2 in the presence of benzylamine, artemisinin transfers an oxygen a tom from the intermediate open hydroperoxide to tertiary amines to form N-o xides and N-benzyl-11-azadesoxyartemisinin Base-catalyzed side reactions in terfere with the corresponding reaction involving dihydroartemisinin. The r eactions serve as a model for biological activity in which the act of bindi ng to a protein liberates hydroperoxide. (C) 1999 Elsevier Science Ltd. All rights reserved.