tert-butyl N-[4-[4-(1,3-dioxobenzo[de]isoquinolin-2-yl)butylamino]butyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]carbamate | 1105486-66-5

• 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: tert-butyl N-[4-[4-(1,3-dioxobenzo[de]isoquinolin-2-yl)butylamino]butyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]carbamate
• CAS: 1105486-66-5
• 化学式: C₃₄H₅₀N₄O₆
• 分子量: 610.794
• InChiKey: QQPMRBLAMLXHJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  44
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[4-[4-(1,3-dioxobenzo[de]isoquinolin-2-yl)butylamino]butyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]carbamate 、 二碳酸二叔丁酯 以 甲醇 为溶剂， 生成 tert-butyl N-[4-(1,3-dioxobenzo[de]isoquinolin-2-yl)butyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonyl-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]amino]butyl]carbamate
  参考文献：
  名称：

  Synthesis, cytotoxicity and apoptosis of naphthalimide polyamine conjugates as antitumor agents

  摘要：

  Several naphthalimide polyamine conjugates were synthesized and evaluated for in vitro cytotoxicity against human leukemia K562, murine melanoma B16, Chinese hamster ovary CHO cell lines. Both triamine moieties and the length of spacers were crucial in elevating the potency of 1,8-naphthalimide. The typical compounds 5a and 5d exhibited excellent cell selectivity to cancer cells through the human hepatoma BEL-7402 and human normal hepatocyte QSG-7701 screens. In addition, 5d could disturb the cell cycle in B16 cells. The research on caspase activity and cytochrome c indicated that 5d could induce B16 cell apoptosis via both the mitochondrial and membrane death receptor pathways, and the Bcl-2 family numbers were involved in the control of apoptosis. (C) 2008 Elsevier Masson SAS. All fights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.044
• 作为产物：
  描述：

  N-(4-bromobutyl)-1,8-naphthalimide 、 tert-butyl (4-aminobutyl)(4-((tert-butoxycarbonyl)amino)butyl)carbamate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 tert-butyl N-[4-[4-(1,3-dioxobenzo[de]isoquinolin-2-yl)butylamino]butyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]carbamate
  参考文献：
  名称：

  Synthesis, cytotoxicity and apoptosis of naphthalimide polyamine conjugates as antitumor agents

  摘要：

  Several naphthalimide polyamine conjugates were synthesized and evaluated for in vitro cytotoxicity against human leukemia K562, murine melanoma B16, Chinese hamster ovary CHO cell lines. Both triamine moieties and the length of spacers were crucial in elevating the potency of 1,8-naphthalimide. The typical compounds 5a and 5d exhibited excellent cell selectivity to cancer cells through the human hepatoma BEL-7402 and human normal hepatocyte QSG-7701 screens. In addition, 5d could disturb the cell cycle in B16 cells. The research on caspase activity and cytochrome c indicated that 5d could induce B16 cell apoptosis via both the mitochondrial and membrane death receptor pathways, and the Bcl-2 family numbers were involved in the control of apoptosis. (C) 2008 Elsevier Masson SAS. All fights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.044

文献信息

• Synthesis, cytotoxicity and apoptosis of naphthalimide polyamine conjugates as antitumor agents
  作者：Zhi-yong Tian、Song-qiang Xie、Yao-wu Du、Yuan-fang Ma、Jin Zhao、Wen-yuan Gao、Chao-jie Wang

  DOI：10.1016/j.ejmech.2008.02.044

  日期：2009.1

  Several naphthalimide polyamine conjugates were synthesized and evaluated for in vitro cytotoxicity against human leukemia K562, murine melanoma B16, Chinese hamster ovary CHO cell lines. Both triamine moieties and the length of spacers were crucial in elevating the potency of 1,8-naphthalimide. The typical compounds 5a and 5d exhibited excellent cell selectivity to cancer cells through the human hepatoma BEL-7402 and human normal hepatocyte QSG-7701 screens. In addition, 5d could disturb the cell cycle in B16 cells. The research on caspase activity and cytochrome c indicated that 5d could induce B16 cell apoptosis via both the mitochondrial and membrane death receptor pathways, and the Bcl-2 family numbers were involved in the control of apoptosis. (C) 2008 Elsevier Masson SAS. All fights reserved.