Journal article

Publication year: 2012

Pages: 6375-6387

Journal: Organic & Biomolecular Chemistry

Volume number: 10

Issue number: 31

ISSN: 1477-0520

eISSN: 1477-0539

Open access status: Green

DOI Link: https://doi.org/10.1039/c2ob25812a

Publisher: Royal Society of Chemistry

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 Ag-II-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 beta-hematin.

Harvard Citation style: Lanfranchi, D., Cesar-Rodo, E., Bertrand, B., Huang, H., Day, L., Johann, L., et al. (2012) Synthesis and biological evaluation of 1,4-naphthoquinones and quinoline-5,8-diones as antimalarial and schistosomicidal agents, Organic and Biomolecular Chemistry, 10(31), pp. 6375-6387. https://doi.org/10.1039/c2ob25812a

APA Citation style: Lanfranchi, D., Cesar-Rodo, E., Bertrand, B., Huang, H., Day, L., Johann, L., Elhabiri, M., Becker, K., Williams, D., & Davioud-Charvet, E. (2012). Synthesis and biological evaluation of 1,4-naphthoquinones and quinoline-5,8-diones as antimalarial and schistosomicidal agents. Organic and Biomolecular Chemistry. 10(31), 6375-6387. https://doi.org/10.1039/c2ob25812a