(+/-)-(3aS,4S,10cS)-2-phenyl-9-methoxy-4-(2,5-dimethoxyphenyl)-3a,4,5,10c-tetrahydro-6H-pyrrolo[3,4-c]carbazole-1,3-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (+/-)-(3aS,4S,10cS)-2-phenyl-9-methoxy-4-(2,5-dimethoxyphenyl)-3a,4,5,10c-tetrahydro-6H-pyrrolo[3,4-c]carbazole-1,3-dione
• 英文别名: (3aS,4S,10cS)-4-(2,5-dimethoxyphenyl)-9-methoxy-2-phenyl-4,5,6,10c-tetrahydro-3aH-pyrrolo[3,4-c]carbazole-1,3-dione
• 化学式: C₂₉H₂₆N₂O₅
• 分子量: 482.536
• InChiKey: AOXPUZWALICHMF-JAMKYWPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-(3aS,4S,10cS)-2-phenyl-9-methoxy-4-(2,5-dimethoxyphenyl)-3a,4,5,10c-tetrahydro-6H-pyrrolo[3,4-c]carbazole-1,3-dione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 3.0h， 以38%的产率得到2-phenyl-9-methoxy-4-(2,5-dimethoxyphenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione
  参考文献：
  名称：

  Open Analogues of Arcyriaflavin A. Synthesis through Diels−Alder Reaction between Maleimides and 1-Aryl-3-tert-butyldimethylsiloxy-1,3-butadienes

  摘要：

  The preparation of a range of open analogues of arcyriaflavin A is described. The synthetic approach is based on the use of perhydroisoindole-1,3,5-triones as key intermediates, which were obtained via Diels-Alder methodology using 1-aryl-3-siloxy-1,3-butadienes as starting materials. Fischer indolization and aromatization processes afforded different methoxy-substituted arylpyrrolocarbazoles. The stereochemistry and conformation of the Diels-Alder products and the regiochemistry of the indolization reactions are supported by NMR and molecular modeling studies.

  DOI：

  10.1021/jo991815x
• 作为产物：
  描述：

  (E)-4-(2,5-dimethoxyphenyl)but-3-en-2-one 在 盐酸 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 苯 为溶剂， 反应 3.0h， 生成 (+/-)-(3aS,4S,10cS)-2-phenyl-9-methoxy-4-(2,5-dimethoxyphenyl)-3a,4,5,10c-tetrahydro-6H-pyrrolo[3,4-c]carbazole-1,3-dione
  参考文献：
  名称：

  Open Analogues of Arcyriaflavin A. Synthesis through Diels−Alder Reaction between Maleimides and 1-Aryl-3-tert-butyldimethylsiloxy-1,3-butadienes

  摘要：

  The preparation of a range of open analogues of arcyriaflavin A is described. The synthetic approach is based on the use of perhydroisoindole-1,3,5-triones as key intermediates, which were obtained via Diels-Alder methodology using 1-aryl-3-siloxy-1,3-butadienes as starting materials. Fischer indolization and aromatization processes afforded different methoxy-substituted arylpyrrolocarbazoles. The stereochemistry and conformation of the Diels-Alder products and the regiochemistry of the indolization reactions are supported by NMR and molecular modeling studies.

  DOI：

  10.1021/jo991815x

文献信息

• Open Analogues of Arcyriaflavin A. Synthesis through Diels−Alder Reaction between Maleimides and 1-Aryl-3-<i>tert</i>-butyldimethylsiloxy-1,3-butadienes
  作者：Marta Adeva、Heidi Sahagún、Esther Caballero、Rafael Peláez-Lamamié de Clairac、Manuel Medarde、Fernando Tomé

  DOI：10.1021/jo991815x

  日期：2000.6.1

  The preparation of a range of open analogues of arcyriaflavin A is described. The synthetic approach is based on the use of perhydroisoindole-1,3,5-triones as key intermediates, which were obtained via Diels-Alder methodology using 1-aryl-3-siloxy-1,3-butadienes as starting materials. Fischer indolization and aromatization processes afforded different methoxy-substituted arylpyrrolocarbazoles. The stereochemistry and conformation of the Diels-Alder products and the regiochemistry of the indolization reactions are supported by NMR and molecular modeling studies.
• Synthesis and cytotoxic activity of different open indolocarbazole alkaloid analogues
  作者：E Caballero

  DOI：10.1016/s0968-0896(03)00308-0

  日期：2003.8.5

  An array of 4-(aryl or indolyl)pyrrolo[3,4-c]carbazole-1,3-diones (open analogues of indolocarbazole alkaloids), 10-(aryl or indolyl)pyrrolo [3,4-b]carbazole-1,3-diones, and different derivatives have been prepared using a Diels-Alder plus Fischer indolization approach and tested as cytotoxic agents. Some representative compounds display interesting cytotoxic profiles. (C) 2003 Elsevier Ltd. All rights reserved.