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- Title
Epiartemisinin, a Remarkably Poor Antimalarial: Implications for the Mode of Action.
- Authors
Jefford, Charles W.; Burger, Ulrich; Millasson-Schmidt, Patricia; Bernardinelli, Gérald; Robinson, Brian L.; Peters, Wallace
- Abstract
Epiartemisinin ( 7) was prepared by the base epimerization of artemisinin ( 1) and its structure determined by X-ray analysis. The antimalarial activity of 7 against the chloroquine-sensitive and resistant strains of Plasmodium berghei and P. yoelii in the mouse was compared with that of the highly effective schizonticide 1 and found to be drastically diminished. It is argued that the mode of action on the intraerythrocytic parasite by 7 is compromised by steric hindrance arising from the α-disposed Me group. In the initial step, intimate complexation with heme is hindered or biased to favor the formation of a less potent C-centered radical, the final lethal agent.
- Publication
Helvetica Chimica Acta, 2000, Vol 83, Issue 6, p1239
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/1522-2675(20000607)83:6<1239::AID-HLCA1239>3.0.CO;2-S