1-(3-methyl-1H-indole)-1,2,3,4-tetrahydro-β-carboline | 168209-33-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-(3-methyl-1H-indole)-1,2,3,4-tetrahydro-β-carboline
• 英文别名: 1-(1H-indol-3-ylmethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS: 168209-33-4
• 化学式: C₂₀H₁₉N₃
• 分子量: 301.391
• InChiKey: CVNDOABNYOTPCC-UHFFFAOYSA-N

物化性质

• 沸点：
  570.8±45.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.61
• 氢给体数：
  3.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(3-methyl-1H-indole)-1,2,3,4-tetrahydro-β-carboline 在 potassium permanganate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以28%的产率得到
  参考文献：
  名称：

  Synthesis of 1-indolyl substituted β-carboline natural products and discovery of antimalarial and cytotoxic activities

  摘要：

  A series of 1-indolyl substituted beta-carbolines including the natural products hyrtiosulawesine, pityriacitrin and pityriacitrin B were prepared via Pictet-Spengler condensation oxidation strategy from the corresponding indolyl-acetaldehydes and substituted tryptamines. Efforts to prepare the C-1 methylene-linked beta-carboline analogues for structure activity relationship studies were unsuccessful. Biological evaluation revealed two analogues (5 and 41) to exhibit weak inhibition of phospholipase A(2) (IC50 171 and 131 mu M, respectively), two to act as antioxidants (3 and 43), and 12 analogues with activity towards a chloroquine-resistant strain (FcB1) of Plasmodium falciparum (IC50 1.0-23 mu M). Testing against a panel of 60 human tumour cell lines revealed a general lack of cytotoxic effect for most of the compounds with the exception of beta-carboline 42 exhibiting modest antileukaemic activity towards the HL-60(TB) cell line (LC50 4.2 mu M). In addition, two novel structures (30 and 32) resulting from aldol condensation followed by Pictet-Spengler cyclisation displayed cytotoxicity with pronounced subpanel specificities towards colon cancer (COLO 205 and HCC-2998) cell lines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.068
• 作为产物：
  描述：

  吲哚-3-乙腈 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 以60%的产率得到1-(3-methyl-1H-indole)-1,2,3,4-tetrahydro-β-carboline
  参考文献：
  名称：

  腈催化氢化过程中吲哚核对亚胺的捕集：四氢-β-咔啉的快速合成

  摘要：

  在乙酸中Pd·C催化加氢后，吲哚乙腈的还原自缩合​​反应生成1-（3-吲哚基甲基）-1,2,3,4-四氢-β-咔啉。氢化3,4-二甲氧基苯基乙腈未能得到四氢罂粟碱，但吲哚乙腈与3,4-二甲氧基苯基乙腈之间的交叉反应可分离出1-（3,4-二甲氧基苄基）-1,2,3,4-四氢-β-咔啉，否则可通过将色胺和3,4-二甲氧基苯基乙腈的混合物催化加氢制得（76％）。除了易于接近育亨宾骨架外，该反应还为四氢-β-咔啉的有用的一般合成方法开辟了道路。

  DOI：

  10.1016/0040-4039(95)00293-l

文献信息

• Trapping of iminiums by the indole nucleus during catalytic hydrogenation of nitriles: a rapid synthesis of tetrahydro-β-carbolines
  作者：Khalid Diker、Michèle Döé de Maindreville、Jean Lévy

  DOI：10.1016/0040-4039(95)00293-l

  日期：1995.4

  Reductive self-condensation of indole acetonitrile upon catalytic hydrogenation over Pd·C in acetic acid yielded 1-(3-indolylmethyl)-1,2,3,4-tetrahydro-β-carboline. Hydrogenating 3,4-dimethoxyphenylacetonitrile failed to give tetrahydropapaverine, but a cross reaction between indole acetonitrile and 3,4-dimethoxyphenylacetonitrile allowed isolation of 1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydro-β-carboline

  在乙酸中Pd·C催化加氢后，吲哚乙腈的还原自缩合​​反应生成1-（3-吲哚基甲基）-1,2,3,4-四氢-β-咔啉。氢化3,4-二甲氧基苯基乙腈未能得到四氢罂粟碱，但吲哚乙腈与3,4-二甲氧基苯基乙腈之间的交叉反应可分离出1-（3,4-二甲氧基苄基）-1,2,3,4-四氢-β-咔啉，否则可通过将色胺和3,4-二甲氧基苯基乙腈的混合物催化加氢制得（76％）。除了易于接近育亨宾骨架外，该反应还为四氢-β-咔啉的有用的一般合成方法开辟了道路。
• Synthesis of 1-indolyl substituted β-carboline natural products and discovery of antimalarial and cytotoxic activities
  作者：Lydia P.P. Liew、Jessica M. Fleming、Arlette Longeon、Elisabeth Mouray、Isabelle Florent、Marie-Lise Bourguet-Kondracki、Brent R. Copp

  DOI：10.1016/j.tet.2014.05.068

  日期：2014.8

  A series of 1-indolyl substituted beta-carbolines including the natural products hyrtiosulawesine, pityriacitrin and pityriacitrin B were prepared via Pictet-Spengler condensation oxidation strategy from the corresponding indolyl-acetaldehydes and substituted tryptamines. Efforts to prepare the C-1 methylene-linked beta-carboline analogues for structure activity relationship studies were unsuccessful. Biological evaluation revealed two analogues (5 and 41) to exhibit weak inhibition of phospholipase A(2) (IC50 171 and 131 mu M, respectively), two to act as antioxidants (3 and 43), and 12 analogues with activity towards a chloroquine-resistant strain (FcB1) of Plasmodium falciparum (IC50 1.0-23 mu M). Testing against a panel of 60 human tumour cell lines revealed a general lack of cytotoxic effect for most of the compounds with the exception of beta-carboline 42 exhibiting modest antileukaemic activity towards the HL-60(TB) cell line (LC50 4.2 mu M). In addition, two novel structures (30 and 32) resulting from aldol condensation followed by Pictet-Spengler cyclisation displayed cytotoxicity with pronounced subpanel specificities towards colon cancer (COLO 205 and HCC-2998) cell lines. (C) 2014 Elsevier Ltd. All rights reserved.