4,9-dihydro-2H-pyrrolo[3,4-g]isoquinoline-4,9-dione

• 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: 4,9-dihydro-2H-pyrrolo[3,4-g]isoquinoline-4,9-dione
• 英文别名: 2H-pyrrolo[3,4-g]isoquinoline-4,9-dione
• 化学式: C₁₁H₆N₂O₂
• 分子量: 198.181
• InChiKey: AOIQVQGHPQHHBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-二甲氨基氯丙烷盐酸盐 、 4,9-dihydro-2H-pyrrolo[3,4-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 2.0h， 以23%的产率得到2-[3-(dimethylamino)propyl]-2H-pyrrolo[3,4-g]isoquinoline-4,9-dione
  参考文献：
  名称：

  新型苯并[f]异吲哚-4,9-二酮类化合物的合成

  摘要：

  摘要描述了具有抗癌活性的单取代和二取代的氮杂萘醌苯并吡咯的设计与合成。在吡咯环上具有各种侧链的N-烷基化反应导致一系列单取代的产物。为了制备二取代的异吲哚衍生物，使用适当取代的甲苯磺酰基甲基异氰化物。针对多种癌细胞系评估了所有化合物的生物活性。 图形概要

  DOI：

  10.1007/s00706-009-0219-2
• 作为产物：
  描述：

  5,5-dimethoxy-5,5-dihydro-8-isoquinolinone 在 对甲基苯磺酰甲基异腈 、 potassium tert-butylate 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 36.0h， 以33%的产率得到4,9-dihydro-2H-pyrrolo[3,4-g]isoquinoline-4,9-dione
  参考文献：
  名称：

  Synthesis of Azanaphthoquinone Annelated Pyrroles

  摘要：

  The synthesis of azanaphthoquinone annelated pyrrole derivatives is described. The [c]-annelated derivative was synthesized by reaction of an azanaphthoquinone monoketal with tosylmethyl isocyanide. The synthesis of each of the two isomeric [b]-annelated pyrrole derivatives was realized by selective acylation reactions with pyrrole. Furthermore detailed NMR spectroscopic studies (H-1,C-13) are published.

  DOI：

  10.3987/com-98-8401

文献信息

• 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 of Azanaphthoquinone Annelated Pyrroles
  作者：Helmut Spreitzer、Andrea Pichler、Wolfgang Holzer、Martin Kratzel、Rita Slanz、Alexandra Koulouri、Petra Krenn、Ulrike Parrer、Petra Szieber

  DOI：10.3987/com-98-8401

  日期：——

  The synthesis of azanaphthoquinone annelated pyrrole derivatives is described. The [c]-annelated derivative was synthesized by reaction of an azanaphthoquinone monoketal with tosylmethyl isocyanide. The synthesis of each of the two isomeric [b]-annelated pyrrole derivatives was realized by selective acylation reactions with pyrrole. Furthermore detailed NMR spectroscopic studies (H-1,C-13) are published.
• Synthesis of new Benzo[f]isoindole-4,9-diones as anticancer compounds
  作者：Nipawan Pongprom、Hans Bachitsch、Arnulf Bauchinger、Hamid Ettefagh、Tanja Haider、Manuela Hofer、Heike Knafl、Rita Slanz、Markus Waismeyer、Friedrich Wieser、Helmut Spreitzer

  DOI：10.1007/s00706-009-0219-2

  日期：2010.1

  AbstractThe design and synthesis of monosubstituted and disubstituted azanaphthoquinone annelated pyrroles with anticancer activity are described. N-alkylation with various side chains at the pyrrole ring led to a series of monosubstituted products. For preparation of disubstituted isoindole derivatives, appropriately substituted tosyl methyl isocyanides were used. The biological activity of all the

  摘要描述了具有抗癌活性的单取代和二取代的氮杂萘醌苯并吡咯的设计与合成。在吡咯环上具有各种侧链的N-烷基化反应导致一系列单取代的产物。为了制备二取代的异吲哚衍生物，使用适当取代的甲苯磺酰基甲基异氰化物。针对多种癌细胞系评估了所有化合物的生物活性。 图形概要