Journal
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume 84, Issue -, Pages 595-604Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2014.07.061
Keywords
8-Hydroxyquinoline; 1,2,3-Triazole; Click reaction; Antiproliferative
Categories
Funding
- CNPq (Conselho Nacional de Desenvolvimento Cientifico e Tecnologico)
- CAPES (Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior)
- FAPEMIG (Fundacao de Amparo a Pesquisa do estado de Minas Gerais)
- PRPq (Pro-Reitoria de Pesquisa da Universidade Federal de Minas Gerais)
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Twelve novel 8-hydroxyquinoline derivatives were synthesized with good yields by performing copper-catalyzed Huisgen 1,3-dipolar cycloaddition (click reaction) between an 8-O-alkylated-quinoline containing a terminal alkyne and various aromatic or protected sugar azides. These compounds were evaluated in vitro for their antiproliferative activity on various cancer cell types. Protected sugar derivative 16 was the most active compound in the series, exhibiting potent antiproliferative activity and high selectivity toward ovarian cancer cells (OVCAR-03, GI(50) < 0.25 mu g mL(-1)); this derivative was more active than the reference drug doxorubicin (OVCAR-03, GI(50) = 0.43 mu g mL(-1)). In structure-activity relationship (SAR) studies, the physico-chemical parameters of the compounds were evaluated and docking calculations were performed for the alpha-glucosidase active site to predict the possible mechanism of action of this series of compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.
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