5-chloro-N-(prop-2-yn-1-yl)-1H-indole-2-carboxamide

• 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: 5-chloro-N-(prop-2-yn-1-yl)-1H-indole-2-carboxamide
• 英文别名: 5-chloro-N-prop-2-ynyl-1H-indole-2-carboxamide
• 化学式: C₁₂H₉ClN₂O
• mdl: MFCD11816209
• 分子量: 232.669
• InChiKey: GNTWCLRMCYHJBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-chloro-N-(prop-2-yn-1-yl)-1H-indole-2-carboxamide 在 zinc trifluoromethanesulfonate 、 caesium carbonate 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 23.0h， 生成 10-chloro-3,6-dimethylimidazo(2’,1’:3,4)pyrazino(1,2-a)indole
  参考文献：
  名称：

  Dual use of propargylamine building blocks in the construction of polyheterocyclic scaffolds

  摘要：

  The cyclization reactions of 2-(N-propargyl)imidazole-2-yl)indoles (synthesized via the hydroamination reaction between N-propargyl indole-2-carboxamides and propargylamine) have been investigated under Lewis acid- and base-promoted conditions. The polyheterocyclic compounds thus obtained were shown to possess promising photophysical properties. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.151970
• 作为产物：
  描述：

  5-氯吲哚-2-羧酸 、 炔丙胺 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以85%的产率得到5-chloro-N-(prop-2-yn-1-yl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  Dual use of propargylamine building blocks in the construction of polyheterocyclic scaffolds

  摘要：

  The cyclization reactions of 2-(N-propargyl)imidazole-2-yl)indoles (synthesized via the hydroamination reaction between N-propargyl indole-2-carboxamides and propargylamine) have been investigated under Lewis acid- and base-promoted conditions. The polyheterocyclic compounds thus obtained were shown to possess promising photophysical properties. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.151970

文献信息

• Structure-activity relationships for binding of 4-substituted triazole-phenols to macrophage migration inhibitory factor (MIF)
  作者：Zhangping Xiao、Marieke Fokkens、Deng Chen、Tjie Kok、Giordano Proietti、Ronald van Merkerk、Gerrit J. Poelarends、Frank J. Dekker

  DOI：10.1016/j.ejmech.2019.111849

  日期：2020.1

  Macrophage migration inhibitory factor (MIF) is a versatile protein that plays a role in inflammation, autoimmune diseases and cancers. Development of novel inhibitors will enable further exploration of MIF as a drug target. In this study, we investigated structure-activity relationships of MIF inhibitors using a MIF tautomerase activity assay to measure binding. Importantly, we notified that transition metals such as copper (II) and zinc (II) interfere with the MIF tautomerase activity under the assay conditions applied. EDTA was added to the assay buffer to avoid interference of residual heavy metals with tautomerase activity measurements. Using these assay conditions the structure-activity relationships for MIF binding of a series of triazole-phenols was explored. The most potent inhibitors in this series provided activities in the low micromolar range. Enzyme kinetic analysis indicates competitive binding that proved reversible. Binding to the enzyme was confirmed using a microscale thermophoresis (MST) assay. Molecular modelling was used to rationalize the observed structure-activity relationships. The most potent inhibitor 2d inhibited proliferation of A549 cells in a clonogenic assay. In addition, 2d attenuated MIF induced ERK phosphorylation in A549 cells. Altogether, this study provides insights in the structure-activity relationships for MIF binding of triazole-phenols and further validates this class of compounds as MIF binding agents in cell-based studies. (C) 2019 The Author(s). Published by Elsevier Masson SAS.
• Dual use of propargylamine building blocks in the construction of polyheterocyclic scaffolds
  作者：Anna Bakholdina、Alexei Lukin、Olga Bakulina、Natalia Guranova、Mikhail Krasavin

  DOI：10.1016/j.tetlet.2020.151970

  日期：2020.6

  The cyclization reactions of 2-(N-propargyl)imidazole-2-yl)indoles (synthesized via the hydroamination reaction between N-propargyl indole-2-carboxamides and propargylamine) have been investigated under Lewis acid- and base-promoted conditions. The polyheterocyclic compounds thus obtained were shown to possess promising photophysical properties. (C) 2020 Elsevier Ltd. All rights reserved.