3,4-diphenyl-9H-pyrido[3,4-b]indole

• 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: 3,4-diphenyl-9H-pyrido[3,4-b]indole
• 化学式: C₂₃H₁₆N₂
• 分子量: 320.393
• InChiKey: AXSDORQJIZAQKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 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：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-[(5,6-Diphenyl-1,2,4-triazin-3-yl)sulfonyl]-1-indol-1-ylethanone 在 lithium aluminium tetrahydride 作用下， 生成 3,4-diphenyl-9H-pyrido[3,4-b]indole
  参考文献：
  名称：

  电子需求逆反应吲哚的Diels-Alder反应。六。与1,2,4-三嗪分子内反应的完全可拆卸的系链

  摘要：

  使用完全可除去的β-磺酰基乙酰基系链将吲哚与1,2,4-三嗪连接，可以通过分子内逆电子需求Diels-Alder反应制备在C1和N9处未取代的β-咔啉。使用2和3氘代吲哚衍生物的机理研究表明，环加成反应会导致[1,5]氢化物移位，并且在脱硫之前会损失N 2。

  DOI：

  10.1016/s0040-4039(98)00379-7

文献信息

• Synthesis of <i>β</i>- and <i>γ</i>-Carbolines by the Palladium-Catalyzed Iminoannulation of Internal Alkynes
  作者：Haiming Zhang、Richard C. Larock

  DOI：10.1021/ol010124w

  日期：2001.10.1

  [GRAPHICS]A variety of substituted beta- and gamma -carbolines have been prepared in good to excellent yields by the annulation of internal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively, in the presence of a palladium catalyst.
• Synthesis of β- and γ-Carbolines by the Palladium-Catalyzed Iminoannulation of Alkynes
  作者：Haiming Zhang、Richard C. Larock

  DOI：10.1021/jo026317u

  日期：2002.12.1

  A variety of substituted beta- and gamma-carbolines have been prepared in moderate to excellent yields by the palladium-catalyzed annulation of internal and terminal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively. This annulation chemistry is effective for a wide range of alkynes, including aryl-, alkyl-, hydroxymethyl-, ethoxycarbonyl-, and trimethylsilyl-substituted alkynes. When an unsymmetrical internal alkyne is employed, this method generally gives two regioisomers. When a terminal alkyne is employed, only one regioisomer has been isolated. This palladium-catalyzed annulation chemistry has also been successfully applied to the synthesis of two biologically interesting beta-carboline alkaloids, ZK93423 and abecarnil (ZK112119).
• Synthesis and cytotoxic activity of 3-phenyl-4-substituted-β-carbolines
  作者：Liu Liu、Ying Ying Xu、Ze Qi Yang、Jian Nan Xiang、Guang Yu Xu

  DOI：10.1016/j.cclet.2012.09.010

  日期：2012.11

  A new class of 3-phenyl-4-substituted-beta carbolines via iodine-mediated electrophilic cyclization as key step were synthesized and their inhibitory activity against three tumor cell lines was evaluated in vitro. It was found that some of the tested compounds showed better cytotoxicity against HeLa and MCF-7 cells than harmine. (C) 2012 Guang Yu Xu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.