3-(1-benzothiophen-3-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione | 221233-60-9

• 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: 3-(1-benzothiophen-3-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione
• CAS: 221233-60-9
• 化学式: C₂₀H₁₂N₂O₂S
• 分子量: 344.393
• InChiKey: DMODZZMXLYIQFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1-benzothiophen-3-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione 在 碘 作用下， 以 苯 为溶剂， 生成 benzo[b]thieno[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H,13H)-dione
  参考文献：
  名称：

  Aryl[ a ]pyrrolo[3,4- c ]carbazoles as selective cyclin D1-CDK4 inhibitors

  摘要：

  The synthesis of new analogues of Arcyriaflavin A in which one indole ring is replaced by an aryl or heteroaryl ring is described. These new series of aryl[a]pyrrolo[3,4-c]carbazoles were evaluated as inhibitors of Cyclin D1-CDK4. A potent and selective D1-CDK4 inhibitor, 7a (D1-CDK4 IC50=45 nM), has been identified. The potency, selectivity profile against other kinases, and structure-activity relationship (SAR) trends of this class of compounds are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00791-1
• 作为产物：
  描述：

  苯并[b]噻吩-3-乙腈 在 氢氧化钾 、 potassium tert-butylate 、 水 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 生成 3-(1-benzothiophen-3-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione
  参考文献：
  名称：

  乙醛酸酯与乙酰胺缩合合成马来酰亚胺的新步骤

  摘要：

  使用1.0 M叔丁醇钾的THF溶液，通过乙醛酸酯与乙酰胺的缩合，可一步制备联苯，二异芳基，吲哚基芳基和吲哚基环烷基马来酰亚胺，收率67-99％。讨论了反应机理。

  DOI：

  10.1016/s0040-4039(98)02594-5

文献信息

• Aryl[ a ]pyrrolo[3,4- c ]carbazoles as selective cyclin D1-CDK4 inhibitors
  作者：Concha Sanchez-Martinez、Chuan Shih、Margaret M. Faul、Guoxin Zhu、Michael Paal、Carmen Somoza、Tiechao Li、Christine A. Kumrich、Leonard L. Winneroski、Zhou Xun、Harold B. Brooks、Bharvin K.R. Patel、Richard M. Schultz、Tammy B. DeHahn、Charles D. Spencer、Scott A. Watkins、Eileen Considine、Jack A. Dempsey、Catherine A. Ogg、Robert M. Campbell、Bryan A. Anderson、Jill Wagner

  DOI：10.1016/s0960-894x(03)00791-1

  日期：2003.11

  The synthesis of new analogues of Arcyriaflavin A in which one indole ring is replaced by an aryl or heteroaryl ring is described. These new series of aryl[a]pyrrolo[3,4-c]carbazoles were evaluated as inhibitors of Cyclin D1-CDK4. A potent and selective D1-CDK4 inhibitor, 7a (D1-CDK4 IC50=45 nM), has been identified. The potency, selectivity profile against other kinases, and structure-activity relationship (SAR) trends of this class of compounds are discussed. (C) 2003 Elsevier Ltd. All rights reserved.
• A new one step synthesis of maleimides by condensation of glyoxylate esters with acetamides
  作者：Margaret M. Faul、Leonard L. Winneroski、Christine A. Krumrich

  DOI：10.1016/s0040-4039(98)02594-5

  日期：1999.2

  Bisphenyl, Bisheteroaryl, indolylaryl and indolylcycloalkyl maleimides are prepared in one step and 67–99% yield by condensation of glyoxylate esters with acetamides using a 1.0 M solution of potassium tert-butoxide in THF. The mechanism of the reaction is discussed.

  使用1.0 M叔丁醇钾的THF溶液，通过乙醛酸酯与乙酰胺的缩合，可一步制备联苯，二异芳基，吲哚基芳基和吲哚基环烷基马来酰亚胺，收率67-99％。讨论了反应机理。
• Synthesis of Aryl- and Heteroaryl[<i>a</i>]pyrrolo[3,4-<i>c</i>]carbazoles
  作者：Concha Sanchez-Martinez、Margaret M. Faul、Chuan Shih、Kevin A. Sullivan、John L. Grutsch、Jeremy T. Cooper、Stanley P. Kolis

  DOI：10.1021/jo034207x

  日期：2003.10.1

  Synthesis of aryl- and hetero[a]pyrrolo[3,4-c]carbazoles by photochemical oxidation and Heck cyclization are described. Photochemical oxidation of 2-naphthyl indolyl maleimide affords two different carbazole regioisomers, depending on the reaction conditions. The regiochemistry of the cyclization can be controlled using the Heck reaction.