2-phenyl-9-methoxy-4-(3,4,5-trimethoxyphenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione | 276680-96-7

• 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: 2-phenyl-9-methoxy-4-(3,4,5-trimethoxyphenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione
• 英文别名: 9-methoxy-2-phenyl-4-(3,4,5-trimethoxyphenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione
• CAS: 276680-96-7
• 化学式: C₃₀H₂₄N₂O₆
• 分子量: 508.53
• InChiKey: RKEZITCHWKFOAD-UHFFFAOYSA-N

物化性质

• 熔点：
  282 °C
• 沸点：
  732.7±70.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-phenyl-9-methoxy-4-(3,4,5-trimethoxyphenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione 在 ammonium hydroxide 、 silver(l) oxide 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 7.0h， 生成 9-methoxy-6-α-D-glucopyranosyl-4-(3,4,5-trimethoxyphenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione
  参考文献：
  名称：

  Synthesis and cytotoxic activity of different open indolocarbazole alkaloid analogues

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(03)00308-0
• 作为产物：
  描述：

  (E)-4-(3,4,5-trimethoxyphenyl)but-3-en-2-one 在 盐酸 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 苯 为溶剂， 反应 6.0h， 生成 2-phenyl-9-methoxy-4-(3,4,5-trimethoxyphenyl)-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.