6-((2-bromoethyl)amino)-2-ethy-1H-benzo[de]isoquinoline-1,3-(2H)-dione | 1448176-36-0

• 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-bromoethyl)amino)-2-ethy-1H-benzo[de]isoquinoline-1,3-(2H)-dione
• CAS: 1448176-36-0
• 化学式: C₁₆H₁₅BrN₂O₂
• 分子量: 347.211
• InChiKey: NXDQUMPKVMTIHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-((2-bromoethyl)amino)-2-ethy-1H-benzo[de]isoquinoline-1,3-(2H)-dione 、 N,N-二甲基乙二胺 在 potassium iodide 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以65%的产率得到6-((2-((2-(dimethylamino)ethyl)amino)ethyl)amino)-2-ethyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Naphthalimides exhibit in vitro antiproliferative and antiangiogenic activities by inhibiting both topoisomerase II (topo II) and receptor tyrosine kinases (RTKs)

  摘要：

  Novel naphthalimide derivatives were designed and synthesized to modulate both topoisomerase II (topo II) and receptor tyrosine kinases (RTKs). Most target compounds exhibited effective and selective antiproliferative activities against three cancer cell lines by inhibiting topo II. The IC50 values ranged from 1.5 to 19.1 mu M. Moreover, compounds 8d and 12d moderately inhibited various angiogenesis-related RTKs, including FGFR1, VEGFR2 and PDGFR alpha. The representative compound 8d was then proved to possess antiangiogenic activity, which was evidenced by the inhibition of migration and tube formation activities of HMEC-1 cells. To our knowledge, it is the first time naphthalimides were identified as tyrosine kinases inhibitors (TKIs) besides their conventional cytotoxicity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.002
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 在 四丁基溴化铵 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 乙二醇甲醚 、 水 为溶剂， 生成 6-((2-bromoethyl)amino)-2-ethy-1H-benzo[de]isoquinoline-1,3-(2H)-dione
  参考文献：
  名称：

  Naphthalimides exhibit in vitro antiproliferative and antiangiogenic activities by inhibiting both topoisomerase II (topo II) and receptor tyrosine kinases (RTKs)

  摘要：

  Novel naphthalimide derivatives were designed and synthesized to modulate both topoisomerase II (topo II) and receptor tyrosine kinases (RTKs). Most target compounds exhibited effective and selective antiproliferative activities against three cancer cell lines by inhibiting topo II. The IC50 values ranged from 1.5 to 19.1 mu M. Moreover, compounds 8d and 12d moderately inhibited various angiogenesis-related RTKs, including FGFR1, VEGFR2 and PDGFR alpha. The representative compound 8d was then proved to possess antiangiogenic activity, which was evidenced by the inhibition of migration and tube formation activities of HMEC-1 cells. To our knowledge, it is the first time naphthalimides were identified as tyrosine kinases inhibitors (TKIs) besides their conventional cytotoxicity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.002