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Title: Novel Endoperoxide Antimalarials: Synthesis, Heme Binding, and Antimalarial Activity
Authors: Taylor, D.K.
Avery, T.D.
Greatrex, B.W.
Tiekink, E.R.T. 
Macreadie, I.G.
Macreadie, P.I.
Humphries, A.D.
Kalkanidis, M.
Fox, E.N.
Klonis, N.
Tilley, L.
Issue Date: 25-Mar-2004
Citation: Taylor, D.K., Avery, T.D., Greatrex, B.W., Tiekink, E.R.T., Macreadie, I.G., Macreadie, P.I., Humphries, A.D., Kalkanidis, M., Fox, E.N., Klonis, N., Tilley, L. (2004-03-25). Novel Endoperoxide Antimalarials: Synthesis, Heme Binding, and Antimalarial Activity. Journal of Medicinal Chemistry 47 (7) : 1833-1839. ScholarBank@NUS Repository.
Abstract: We report the synthesis of a series of novel epoxy endoperoxide compounds that can be prepared in high yields in one to three steps from simple starting materials. Some of these compounds inhibit the growth of Plasmodium falciparum in vitro. Structure-activity studies indicate that an endoperoxide ring bisubstituted with saturated cyclic moieties is the pharmacophore. To study the molecular basis of the action of these novel antimalarial compounds, we examined their ability to interact with oxidized and reduced forms of heme. Some of the compounds interact with oxidized heme in a fashion similar to chloroquine and other 4-aminoquinolines, while some of the compounds interact with reduced heme. However, the level of antimalarial potency is not well correlated with these activities, suggesting that some of the endoperoxides may exert their antimalarial activities by a novel mechanism of action.
Source Title: Journal of Medicinal Chemistry
ISSN: 00222623
DOI: 10.1021/jm0305319
Appears in Collections:Staff Publications

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