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Novel endoperoxide antimalarials: synthesis, heme binding, and antimalarial activity

Taylor, Dennis K., Avery, Thomas D., Greatrex, Ben W., Tiekink, Edward R.T., Macreadie, Ian G., Macreadie, Peter I., Humphries, Adam D., Kalkanidis, Martha, Fox, Emma N., Klonis, Nectarios and Tilley, Leann 2004, Novel endoperoxide antimalarials: synthesis, heme binding, and antimalarial activity, Journal of medicinal chemistry, vol. 47, no. 7, pp. 1833-1839, doi: 10.1021/jm0305319.

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Title Novel endoperoxide antimalarials: synthesis, heme binding, and antimalarial activity
Author(s) Taylor, Dennis K.
Avery, Thomas D.
Greatrex, Ben W.
Tiekink, Edward R.T.
Macreadie, Ian G.
Macreadie, Peter I.ORCID iD for Macreadie, Peter I. orcid.org/0000-0001-7362-0882
Humphries, Adam D.
Kalkanidis, Martha
Fox, Emma N.
Klonis, Nectarios
Tilley, Leann
Journal name Journal of medicinal chemistry
Volume number 47
Issue number 7
Start page 1833
End page 1839
Total pages 7
Publisher American Chemical Society
Place of publication Washington, D.C.
Publication date 2004
ISSN 0022-2623
Summary 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.
Language eng
DOI 10.1021/jm0305319
Field of Research 030503 Organic Chemical Synthesis
Socio Economic Objective 860803 Human Pharmaceutical Treatments (e.g. Antibiotics)
HERDC Research category C1.1 Refereed article in a scholarly journal
Copyright notice ©2004, American Chemical Society
Persistent URL http://hdl.handle.net/10536/DRO/DU:30076251

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