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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

par Madonna, Sébastien;Marcowycz, Aline ;Lamoral-Theys, Delphine ;Van Goietsenoven, Gwendoline ;Dessolin, Jean;Pirker, Christine;Spiegl-Kreinecker, Sabine;Biraboneye, César-Alain;Berger, Walter;Kiss, Robert ;Krausa, Jean-Louis
Référence Journal of heterocyclic chemistry, 47, 3, page (719-723)
Publication Publié, 2010-05

Article révisé par les pairs

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Résumé :

(Chemical Equation Presented) 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. © 2010 HeteroCorporation.