8-(3-(1-(4-iodobenzyl)-1H-1,2,3-triazol-4-yl)propoxy)quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-(3-(1-(4-iodobenzyl)-1H-1,2,3-triazol-4-yl)propoxy)quinoline
• 英文别名: 8-[3-[1-[(4-Iodophenyl)methyl]triazol-4-yl]propoxy]quinoline；8-[3-[1-[(4-iodophenyl)methyl]triazol-4-yl]propoxy]quinoline
• 化学式: C₂₁H₁₉IN₄O
• 分子量: 470.313
• InChiKey: LRCZGHZWGLNJJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-碘苄醇 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 16.5h， 生成 8-(3-(1-(4-iodobenzyl)-1H-1,2,3-triazol-4-yl)propoxy)quinoline
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.07.061

文献信息

• Synthesis and antiproliferative activity of 8-hydroxyquinoline derivatives containing a 1,2,3-triazole moiety
  作者：Luiza B. de O. Freitas、Thiago F. Borgati、Rossimiriam P. de Freitas、Ana L.T.G. Ruiz、Gabriela M. Marchetti、João E. de Carvalho、Elaine F.F. da Cunha、Teodorico C. Ramalho、Rosemeire B. Alves

  DOI：10.1016/j.ejmech.2014.07.061

  日期：2014.9

  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.