1-(1H-indol-3-yl)-9H-pyrido[3,4-b]indole-3-carboxylic acid

• 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-(1H-indol-3-yl)-9H-pyrido[3,4-b]indole-3-carboxylic acid
• 英文别名: eudistomin U 3-carboxylic acid
• 化学式: C₂₀H₁₃N₃O₂
• 分子量: 327.342
• InChiKey: HXKHQONVLOTGLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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：
  81.8
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1H-indol-3-yl)-9H-pyrido[3,4-b]indole-3-carboxylic acid 在 喹啉 、 铜 作用下， 反应 0.17h， 以88%的产率得到eudistomin U
  参考文献：
  名称：

  通过钌和铑催化的炔属酰胺与氰基甲酸酯的[2 + 2 + 2]环加成反应合成β-和γ-咔啉。

  摘要：

  描述了一种基于过渡金属催化的功能化炔属酰胺与甲基氰基甲酸酯之间的[2 + 2 + 2]环加成反应的灵活方法，用于取代β-和γ-咔啉。该新反应序列的多功能性通过其在海洋天然产物eudistomin U的全合成中的应用得以证明。

  DOI：

  10.1039/c1cc11298h
• 作为产物：
  描述：

  N-(2-ethynylphenyl)-4-methyl-N-[2-[1-(4-methylphenyl)sulfonylindol-3-yl]ethynyl]benzenesulfonamide 在 chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(1H-indol-3-yl)-9H-pyrido[3,4-b]indole-3-carboxylic acid
  参考文献：
  名称：

  通过钌和铑催化的炔属酰胺与氰基甲酸酯的[2 + 2 + 2]环加成反应合成β-和γ-咔啉。

  摘要：

  描述了一种基于过渡金属催化的功能化炔属酰胺与甲基氰基甲酸酯之间的[2 + 2 + 2]环加成反应的灵活方法，用于取代β-和γ-咔啉。该新反应序列的多功能性通过其在海洋天然产物eudistomin U的全合成中的应用得以证明。

  DOI：

  10.1039/c1cc11298h

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.
• An iminophosphorane-mediated efficient synthesis of the alkaloid eudistomin U of marine origin
  作者：Pedro Molina、Pilar M. Fresneda、Sagrario García-Zafra

  DOI：10.1016/0040-4039(95)00565-t

  日期：1995.5

  The first synthesis of the alkaloid eudistomin U, by a four-step sequence is described. The key step,formation of the beta-carboline ring, involves a tandem aza Wittig/electrocyclic ring closure process.
• 3-Amide-β-carbolines block the cell cycle by targeting CDK2 and DNA in tumor cells potentially as anti-mitotic agents
  作者：Dongming Zhi、Zhiyuan An、Lishan Li、Chaojia Zheng、Xiaorong Yuan、Yu Lan、Jinghan Zhang、Yujie Xu、Huiya Ma、Na Li、Junru Wang

  DOI：10.1016/j.bioorg.2024.107216

  日期：2024.4
• Synthesis of β- and γ-carbolines via ruthenium and rhodium catalysed [2+2+2] cycloadditions of yne-ynamides with methylcyanoformate
  作者：Felix Nissen、Vincent Richard、Carole Alayrac、Bernhard Witulski

  DOI：10.1039/c1cc11298h

  日期：——

  towards substituted beta- and gamma-carbolines based on transition metal catalysed [2+2+2] cycloaddition reactions between functionalised yne-ynamides and methylcyanoformate is described. The versatility of this new reaction sequence is demonstrated by its application in the total synthesis of the marine natural product eudistomin U.

  描述了一种基于过渡金属催化的功能化炔属酰胺与甲基氰基甲酸酯之间的[2 + 2 + 2]环加成反应的灵活方法，用于取代β-和γ-咔啉。该新反应序列的多功能性通过其在海洋天然产物eudistomin U的全合成中的应用得以证明。