1-[2-(Dimethylamino)ethyl]pyrrolo[3,2-g]isoquinoline-4,9-dione | 957199-68-7

• 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: 1-[2-(Dimethylamino)ethyl]pyrrolo[3,2-g]isoquinoline-4,9-dione
• CAS: 957199-68-7
• 化学式: C₁₅H₁₅N₃O₂
• 分子量: 269.303
• InChiKey: BLQFVFZLGNIHMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-(Dimethylamino)ethyl]pyrrolo[3,2-g]isoquinoline-4,9-dione 在 氢氧化钾 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of novel cytotoxic azanaphthoquinone annelated pyrrolo oximes

  摘要：

  Two series of azanaphthoquinone annelated pyrrolo oximes have been synthesized. The antiproliferative activities of 10 compounds were evaluated on at least four different cell lines. One series of pyrrolo derivatives showed high cytotoxic activity. The effects on cell cycle and caspase activity were investigated. Compounds 9a and 9b showed an accumulation of cells in G2/M phase. Substantial and dose-dependent caspase activity was found after treatment of cells with 9a and 9b. This indicates an apoptosis inducing property of these compounds. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.09.054
• 作为产物：
  描述：

  二甲氨基氯乙烷盐酸 、 1H-pyrrolo[3,2-g]isoquinoline-4,9-dione 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以48%的产率得到1-[2-(Dimethylamino)ethyl]pyrrolo[3,2-g]isoquinoline-4,9-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel cytotoxic azanaphthoquinone annelated pyrrolo oximes

  摘要：

  Two series of azanaphthoquinone annelated pyrrolo oximes have been synthesized. The antiproliferative activities of 10 compounds were evaluated on at least four different cell lines. One series of pyrrolo derivatives showed high cytotoxic activity. The effects on cell cycle and caspase activity were investigated. Compounds 9a and 9b showed an accumulation of cells in G2/M phase. Substantial and dose-dependent caspase activity was found after treatment of cells with 9a and 9b. This indicates an apoptosis inducing property of these compounds. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.09.054

文献信息

• Synthesis of anticancer compounds, III (Bioorg Med Chem Lett 17, 6091, 2007), carbinol derivatives of azanaphthoquinone annelated pyrroles
  作者：Nipawan Pongprom、Gerhard Müller、Peter Schmidt、Wolfgang Holzer、Helmut Spreitzer

  DOI：10.1007/s00706-008-0024-3

  日期：2009.3

  A series of carbinols has been synthesized by attachment of different piperidinyl side chains to the quinone structure of azanaphthoquinone annelated pyrroles. The synthesized compounds were screened for their cytotoxic activities. Compared to previously published results, they exhibited only moderate activities, thus showing that the existence of the quinone moiety seems to be essential for anticancer activities of this group.
• Synthesis and biological evaluation of novel cytotoxic azanaphthoquinone annelated pyrrolo oximes
  作者：Karem Shanab、Nipawan Pongprom、Eva Wulz、Wolfgang Holzer、Helmut Spreitzer、Peter Schmidt、Babette Aicher、Gilbert Müller、Eckhard Günther

  DOI：10.1016/j.bmcl.2007.09.054

  日期：2007.11

  Two series of azanaphthoquinone annelated pyrrolo oximes have been synthesized. The antiproliferative activities of 10 compounds were evaluated on at least four different cell lines. One series of pyrrolo derivatives showed high cytotoxic activity. The effects on cell cycle and caspase activity were investigated. Compounds 9a and 9b showed an accumulation of cells in G2/M phase. Substantial and dose-dependent caspase activity was found after treatment of cells with 9a and 9b. This indicates an apoptosis inducing property of these compounds. (C) 2007 Published by Elsevier Ltd.
• Synthesis and biological evaluation of new cytotoxic azanaphthoquinone pyrrolo-annelated derivatives
  作者：Karem Shanab、Eva Schirmer、Heike Knafl、Eva Wulz、Wolfgang Holzer、Helmut Spreitzer、Peter Schmidt、Babette Aicher、Gilbert Müller、Eckhard Günther

  DOI：10.1016/j.bmcl.2010.05.003

  日期：2010.7

  A series of azanaphthoquinone pyrrolo-annelated derivatives attached to basic side chains have been synthesized. The antiproliferative activities of all compounds were evaluated on at least four different cell lines. The effects on cell cycle and intercalation were investigated. (c) 2010 Elsevier Ltd. All rights reserved.