کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1395634 1501132 2014 10 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis and antiproliferative activity of 8-hydroxyquinoline derivatives containing a 1,2,3-triazole moiety
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Synthesis and antiproliferative activity of 8-hydroxyquinoline derivatives containing a 1,2,3-triazole moiety
چکیده انگلیسی


• 8-Hydroxyquinoline derivatives containing a 1,2,3-triazole moiety were synthesized.
• The compounds were evaluated in vitro for their antiproliferative activity.
• Physico-chemical parameters were calculated through SAR studies.
• Docking calculations were performed for the α-glucosidase active site.

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.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: European Journal of Medicinal Chemistry - Volume 84, 12 September 2014, Pages 595–604
نویسندگان
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