Exploring the trifluoromenadione core as a template to design antimalarial redox-active agents interacting with glutathione reductase
Menadione is the 2-methyl-1,4-naphthoquinone core used to design potent antimalarial redox-cyclers to affect the redox equilibrium of Plasmodium-infected red blood cells. Exploring the reactivity of fluoromethyl-1,4-naphthoquinones, in particular trifluoromenadione, under quasi-physiological conditi...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
17 Apr 2012
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| In: |
Organic & biomolecular chemistry
Year: 2012, Volume: 10, Issue: 24, Pages: 4795-4806 |
| ISSN: | 1477-0539 |
| DOI: | 10.1039/C2OB25229E |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1039/C2OB25229E Verlag, Volltext: https://pubs.rsc.org/en/content/articlelanding/2012/ob/c2ob25229e 
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| Author Notes: | Don Antoine Lanfranchi, Didier Belorgey, Tobias Müller, Hervé Vezin, Michael Lanzer, Elisabeth Davioud-Charvet |
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| 520 | |a Menadione is the 2-methyl-1,4-naphthoquinone core used to design potent antimalarial redox-cyclers to affect the redox equilibrium of Plasmodium-infected red blood cells. Exploring the reactivity of fluoromethyl-1,4-naphthoquinones, in particular trifluoromenadione, under quasi-physiological conditions in NADPH-dependent glutathione reductase reactions, is discussed in terms of chemical synthesis, electrochemistry, enzyme kinetics, and antimalarial activities. Multitarget-directed drug discovery is an emerging approach to the design of new antimalarial drugs. Combining in one single 1,4-naphthoquinone molecule, the trifluoromenadione core with the alkyl chain at C-3 of the known antimalarial drug atovaquone, revealed a mechanism for CF3 as a leaving group. The resulting trifluoromethyl derivative 5 showed a potent antimalarial activity per se against malarial parasites in culture. | ||
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