6-[2-(4-methoxyphenyl)ethyl]-9-[(2-morpholin-4-ylethyl)amino]pyrido[2',1':2,3]imidazo [4,5-c]isoquinolin-5(6H)-one | 1228832-01-6

• 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: 6-[2-(4-methoxyphenyl)ethyl]-9-[(2-morpholin-4-ylethyl)amino]pyrido[2',1':2,3]imidazo [4,5-c]isoquinolin-5(6H)-one
• 英文别名: 9-[2-(4-Methoxyphenyl)ethyl]-13-(2-morpholin-4-ylethylamino)-9,11,17-triazatetracyclo[8.7.0.02,7.011,16]heptadeca-1(10),2,4,6,12,14,16-heptaen-8-one
• CAS: 1228832-01-6
• 化学式: C₂₉H₃₁N₅O₃
• 分子量: 497.597
• InChiKey: XZGVUFDRHKFZIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(2-氨基乙基)吗啉 、 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68%的产率得到6-[2-(4-methoxyphenyl)ethyl]-9-[(2-morpholin-4-ylethyl)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

文献信息

• 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
  作者：Tao Meng、Wei Wang、Zhixiang Zhang、Lanping Ma、Yongliang Zhang、Zehong Miao、Jingkang Shen

  DOI：10.1016/j.bmc.2013.12.004

  日期：2014.1

  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.