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Title: Novel Endoperoxide Antimalarials: Synthesis, Heme Binding, and Antimalarial Activity
Contributor(s): Taylor, Dennis K (author); Avery, Thomas D (author); Tilley, Leann (author); Greatrex, Ben  (author)orcid ; Tiekink, Edward R T (author); Macreadie, Ian G (author); Macreadie, Peter I (author); Humphries, Adam D (author); Kalkanidis, Martha (author); Fox, Emma N (author); Klonis, Nectarios (author)
Publication Date: 2004
DOI: 10.1021/jm0305319
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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.
Publication Type: Journal Article
Source of Publication: Journal of Medicinal Chemistry, 47(7), p. 1833-1839
Publisher: American Chemical Society
Place of Publication: United States of America
ISSN: 0022-2623
Field of Research (FOR): 030401 Biologically Active Molecules
030503 Organic Chemical Synthesis
Socio-Economic Objective (SEO): 970103 Expanding Knowledge in the Chemical Sciences
929999 Health not elsewhere classified
970106 Expanding Knowledge in the Biological Sciences
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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