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Synthesis and antiproliferative activity of 8-hydroxyquinoline derivatives containing a 1,2,3-triazole moiety.

Abstract：

: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, GI50 < 0.25 μg mL(-1)); this derivative was more active than the reference drug doxorubicin (OVCAR-03, GI50 = 0.43 μg mL(-1)). In structure-activity relationship (SAR) studies, the physico-chemical parameters of the compounds were evaluated and docking calculations were performed for the α-glucosidase active site to predict the possible mechanism of action of this series of compounds.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Freitas LB,Borgati TF,de Freitas RP,Ruiz AL,Marchetti GM,de Carvalho JE,da Cunha EF,Ramalho TC,Alves RB

doi

10.1016/j.ejmech.2014.07.061

subject

Has Abstract

pub_date

2014-09-12 00:00:00

pages

595-604

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(14)00676-X

journal_volume

84

pub_type

杂志文章

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