(E)-1-(1,3-diphenylprop-1-en-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole | 1616670-81-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(1,3-diphenylprop-1-en-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 英文别名: 1-[(E)-1,3-diphenylprop-1-enyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS: 1616670-81-5
• 化学式: C₂₆H₂₄N₂
• 分子量: 364.49
• InChiKey: MHITUHWXSQZHCD-LTGZKZEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯乙醛 在 ammonium acetate 作用下， 以 水 、 溶剂黄146 、 乙酸乙酯 、 甲苯 为溶剂， 反应 3.0h， 生成 (E)-1-(1,3-diphenylprop-1-en-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  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

文献信息

• 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.