9-bromo-6-(4-methoxyphenethyl)pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one | 1228832-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 9-bromo-6-(4-methoxyphenethyl)pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one
• CAS: 1228832-06-1
• 化学式: C₂₃H₁₈BrN₃O₂
• 分子量: 448.319
• InChiKey: JDIMKURCPYPGCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  48.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-甲氨基吡啶 、 9-bromo-6-(4-methoxyphenethyl)pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one 在 copper(l) iodide 、 potassium carbonate 、 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以56%的产率得到6-[2-(4-methoxyphenyl)ethyl]-9-[(pyridin-4-ylmethyl)amino]pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 6H-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-ones as antimitotic agents and inhibitors of tubulin polymerization

  摘要：

  A series of 6H-pyrido[20,10: 2,3] imidazo[4,5-c] isoquinolin-5(6H)-ones have been synthesized and evaluated for their antiproliferative activities. Among them, compounds 2j and 4d displayed potent cytotoxic activities in vitro against HeLa cell line with IC50 values of 0.07 and 0.06 mu M, respectively. In general, the antiproliferative activities are correlated with the inhibitory effect on tubulin polymerization and binding property of the colchicine binding site. In addition, flow cytometry and immunofluorescence analysis revealed selected compounds caused G2/M phase arrest of the cell cycle and disruption of the mitotic spindle assembly, which had correlation with proliferation inhibitory activity. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.12.004