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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
Author(s) -
Madonna Sébastien,
Marcowycz Aline,
LamoralTheys Delphine,
Van Goietsenoven Gwendoline,
Dessolin Jean,
Pirker Christine,
SpieglKreinecker Sabine,
Biraboneye CésarAlain,
Berger Walter,
Kiss Robert,
Kraus JeanLouis
Publication year - 2010
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.304
Subject(s) - chemistry , stereochemistry , methyl group , 8 hydroxyquinoline , ring (chemistry) , medicinal chemistry , group (periodic table) , organic chemistry
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).