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Issue 31, 2012
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Synthesis and biological evaluation of 1,4-naphthoquinones and quinoline-5,8-diones as antimalarial and schistosomicidal agents

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Abstract

Improving the solubility of polysubstituted 1,4-naphthoquinone derivatives was achieved by introducing nitrogen in two different positions of the naphthoquinone core, at C-5 and at C-8 of menadione through a two-step, straightforward synthesis based on the regioselective hetero-Diels–Alder reaction. The antimalarial and the antischistosomal activities of these polysubstituted aza-1,4-naphthoquinone derivatives were evaluated and led to the selection of distinct compounds for antimalarial versus antischistosomal action. The AgII-assisted oxidative radical decarboxylation of the phenyl acetic acids using AgNO3 and ammonium peroxodisulfate was modified to generate the 3-picolinyl-menadione with improved pharmacokinetic parameters, high antimalarial effects and capacity to inhibit the formation of β-hematin.

Graphical abstract: Synthesis and biological evaluation of 1,4-naphthoquinones and quinoline-5,8-diones as antimalarial and schistosomicidal agents

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Article information


Submitted
27 Apr 2012
Accepted
14 Jun 2012
First published
14 Jun 2012

Org. Biomol. Chem., 2012,10, 6375-6387
Article type
Paper

Synthesis and biological evaluation of 1,4-naphthoquinones and quinoline-5,8-diones as antimalarial and schistosomicidal agents

D. A. Lanfranchi, E. Cesar-Rodo, B. Bertrand, H. Huang, L. Day, L. Johann, M. Elhabiri, K. Becker, D. L. Williams and E. Davioud-Charvet, Org. Biomol. Chem., 2012, 10, 6375
DOI: 10.1039/C2OB25812A

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