methyl 1-(1H-indol-3-yl)-β-carboline-3-carboxylate | 1242336-86-2

• 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: methyl 1-(1H-indol-3-yl)-β-carboline-3-carboxylate
• 英文别名: methyl 1-(1H-indol-3-yl)-9H-pyrido[3,4-b]indole-3-carboxylate；Methyl 1-(1H-indol-3-yl)-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1242336-86-2
• 化学式: C₂₁H₁₅N₃O₂
• 分子量: 341.369
• InChiKey: CKXWMAVCKHNJRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  70.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-(1H-indol-3-yl)-β-carboline-3-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 13.0h， 以96%的产率得到1-(1H-indol-3-yl)-9H-pyrido[3,4-b]indole-3-carboxylic acid
  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：

  methyl 1-(1H-indol-3-yl)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate 在 四丁基溴化铵 、 2-碘酰基苯甲酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以71%的产率得到methyl 1-(1H-indol-3-yl)-β-carboline-3-carboxylate
  参考文献：
  名称：

  Room-Temperature Aromatization of Tetrahydro-β-carbolines by 2-Iodoxybenzoic Acid: Utility in a Total Synthesis of Eudistomin U

  摘要：

  2-Iodoxybenzoic acid is a convenient reagent for the dehydrogenation of tetrahydro-beta-carbolines to their aromatic forms under mild conditions. The utility of the method was demonstrated in a total synthesis of the marine indole alkaloid eudistomin U.

  DOI：

  10.1021/ol101688x

文献信息

• Room-Temperature Aromatization of Tetrahydro-β-carbolines by 2-Iodoxybenzoic Acid: Utility in a Total Synthesis of Eudistomin U
  作者：Joseph D. Panarese、Stephen P. Waters

  DOI：10.1021/ol101688x

  日期：2010.9.17

  2-Iodoxybenzoic acid is a convenient reagent for the dehydrogenation of tetrahydro-beta-carbolines to their aromatic forms under mild conditions. The utility of the method was demonstrated in a total synthesis of the marine indole alkaloid eudistomin U.
• 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.