Bis-8-hydroxyquinoline and bis-8-hydroxyquinaldine N-substituted amines: A single methyl group structural difference between the two heterocycles, which modulates the antiproliferative effects

The synthesis of a series of bis‐8‐hydroxyquinoline‐ and bis‐8‐hydroxyquinaldine‐substituted N‐benzyl or thiophenyl amines and their corresponding bis‐8‐hydroxyquinoline is reported. In vitro growth inhibitory effects of both series have been evaluated. It has been observed that analogs from the bis...

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Published in:Journal of heterocyclic chemistry 2010-05, Vol.47 (3), p.719-723
Main Authors: Madonna, Sébastien, Marcowycz, Aline, Lamoral-Theys, Delphine, Van Goietsenoven, Gwendoline, Dessolin, Jean, Pirker, Christine, Spiegl-Kreinecker, Sabine, Biraboneye, César-Alain, Berger, Walter, Kiss, Robert, Kraus, Jean-Louis
Format: Article
Language:English
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Summary:The synthesis of a series of bis‐8‐hydroxyquinoline‐ and bis‐8‐hydroxyquinaldine‐substituted N‐benzyl or thiophenyl amines and their corresponding bis‐8‐hydroxyquinoline is reported. In vitro growth inhibitory effects of both series have been evaluated. It has been observed that analogs from the bis‐8‐hydroxyquinoline series exert nanomolar range activity, whereas the antiproliferative activity of the corresponding analogs from the bis‐8‐hydroxyquinaldine series was found to be drastically lower. Molecular docking and chemical–physical properties account for these observed growth inhibitory differences between the two series of analogs, which differ only by the presence of a methyl group at the 2 position of the heterocyclic ring. J. Heterocyclic Chem., (2010).
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.304