Issue 31, 2012

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

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

Supplementary files

Article information

Article type
Paper
Submitted
27 Apr 2012
Accepted
14 Jun 2012
First published
14 Jun 2012

Org. Biomol. Chem., 2012,10, 6375-6387

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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