2,3,4,5-tetrahydro-8-methanesulfonyl-2-(phenylmethyl)-1H-pyrido[4,3-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: 2,3,4,5-tetrahydro-8-methanesulfonyl-2-(phenylmethyl)-1H-pyrido[4,3-b]indole
• 英文别名: 2-benzyl-8-methanesulfonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；2-Benzyl-8-methylsulfonyl-1,3,4,5-tetrahydropyrido[4,3-b]indole
• 化学式: C₁₉H₂₀N₂O₂S
• 分子量: 340.446
• InChiKey: QOGPBIAQOIPEGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetrahydro-8-methanesulfonyl-2-(phenylmethyl)-1H-pyrido[4,3-b]indole 、 苯甲酰氯 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 、 水 、 乙酸乙酯 为溶剂， 以30%的产率得到5-benzoyl-2-benzyl-8-methanesulfonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  Synthesis and biological activity of N-aroyl-tetrahydro-γ-carbolines

  摘要：

  Research on dual inhibitors of both 5-LOX and COXs gained interest due to the overexpressions of these enzymes during the malignant state of the evolution of prostate cancer. In order to take part in this research, new N-aroyl-tetrahydro-gamma-carbolines issued from the modi. cation of Indomethacin have been synthesised. As for the NSAIDs, the compounds have been tested for their activity against COX1, COX2 plus against 5-LOX and against the proliferation of malignant prostate cancer. Interesting cytotoxic activities and selectivities of some tetrahydro-gamma-carboline derivatives have been obtained. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.034
• 作为产物：
  描述：

  4-溴苯肼盐酸盐 在 盐酸 、 sodium hydroxide 、 copper(l) iodide 、 L-脯氨酸 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 51.0h， 生成 2,3,4,5-tetrahydro-8-methanesulfonyl-2-(phenylmethyl)-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  8-取代的四氢-γ-咔啉的合成

  摘要：

  使用催化或热方法，将Fischer反应应用于具有供电子或吸电子基团的8-取代的四氢-γ-咔啉的合成。反应条件必须根据哌啶酮的N 1取代基的性质而变化。当芳基肼上的释放基团和哌啶酮的氮上的苄基取代基存在时，观察到最好的结果。在软酸性条件下观察到带有取代基的咔啉的形成；在其他情况下，反应在ended水平结束或没有发生。

  DOI：

  10.1002/jhet.5570430308

文献信息

• Synthesis and biological activity of N-aroyl-tetrahydro-γ-carbolines
  作者：Alexandre Bridoux、Régis Millet、Jean Pommery、Nicole Pommery、Jean-Pierre Henichart

  DOI：10.1016/j.bmc.2010.04.034

  日期：2010.6.1

  Research on dual inhibitors of both 5-LOX and COXs gained interest due to the overexpressions of these enzymes during the malignant state of the evolution of prostate cancer. In order to take part in this research, new N-aroyl-tetrahydro-gamma-carbolines issued from the modi. cation of Indomethacin have been synthesised. As for the NSAIDs, the compounds have been tested for their activity against COX1, COX2 plus against 5-LOX and against the proliferation of malignant prostate cancer. Interesting cytotoxic activities and selectivities of some tetrahydro-gamma-carboline derivatives have been obtained. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of 8-substituted tetrahydro-γ-carbolines
  作者：Alexandre Bridoux、Laurence Goossens、Raymond Houssin、Jean-Pierre Héanichart

  DOI：10.1002/jhet.5570430308

  日期：2006.5

  The Fischer reaction is applied to the synthesis of 8-substituted tetrahydro-γ-carbolines with electron-donating or electron-withdrawing groups, using catalytic or thermal methods. The reaction conditions must be varied according to the nature of the N 1 substituent of the piperidone. The best results are observed when a releasing group is present on the arylhydrazine and a benzyl substituent on the

  使用催化或热方法，将Fischer反应应用于具有供电子或吸电子基团的8-取代的四氢-γ-咔啉的合成。反应条件必须根据哌啶酮的N 1取代基的性质而变化。当芳基肼上的释放基团和哌啶酮的氮上的苄基取代基存在时，观察到最好的结果。在软酸性条件下观察到带有取代基的咔啉的形成；在其他情况下，反应在ended水平结束或没有发生。