1-methyl-2-((methylamino)methyl)-1H-indol-5-ol | 130081-92-4

• 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: 1-methyl-2-((methylamino)methyl)-1H-indol-5-ol
• 英文别名: 1-Methyl-2-(methylaminomethyl)indol-5-ol
• CAS: 130081-92-4
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: PEQHLXSOPQUHIO-UHFFFAOYSA-N

物化性质

• 沸点：
  366.9±27.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-2-((methylamino)methyl)-1H-indol-5-ol 在 sodium hydride 、 叔丁胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.08h， 生成 N-((5-((8-methoxyquinolin-5-yl)methoxy)-1-methyl-1H-indol-2-yl)methyl)-Nmethylprop-2-yn-1-amine
  参考文献：
  名称：

  N-Methyl-N-((1-methyl-5-(3-(1-(2-methylbenzyl)piperidin-4-yl)propoxy)-1H-indol-2-yl)methyl)prop-2-yn-1-amine, a New Cholinesterase and Monoamine Oxidase Dual Inhibitor

  摘要：

  On the basis of N-((5-(3-(1-benzylpiperidin-4-yl)propoxy)-1-methyl-1H-indol-2-yl)methyl)-N-methylprop-2-yn-1-amine (II, ASS234) and QSAR predictions, in this work we have designed, synthesized, and evaluated a number of new indole derivatives from which we have identified N-methyl-N-((1-methyl-5-(3-(1-(2-methylbenzyl)piperidin-4-yl)propoxy)-1H-indol-2-yl)methyl)prop-2-yn-1-amine (2, MBA236) as a new cholinesterase and monoamine oxidase dual inhibitor.

  DOI：

  10.1021/jm501501a
• 作为产物：
  描述：

  [(5-甲氧基-1H-吲哚-2-基)甲基]甲胺 在 三溴化硼 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 48.0h， 以80%的产率得到1-methyl-2-((methylamino)methyl)-1H-indol-5-ol
  参考文献：
  名称：

  N-Methyl-N-((1-methyl-5-(3-(1-(2-methylbenzyl)piperidin-4-yl)propoxy)-1H-indol-2-yl)methyl)prop-2-yn-1-amine, a New Cholinesterase and Monoamine Oxidase Dual Inhibitor

  摘要：

  On the basis of N-((5-(3-(1-benzylpiperidin-4-yl)propoxy)-1-methyl-1H-indol-2-yl)methyl)-N-methylprop-2-yn-1-amine (II, ASS234) and QSAR predictions, in this work we have designed, synthesized, and evaluated a number of new indole derivatives from which we have identified N-methyl-N-((1-methyl-5-(3-(1-(2-methylbenzyl)piperidin-4-yl)propoxy)-1H-indol-2-yl)methyl)prop-2-yn-1-amine (2, MBA236) as a new cholinesterase and monoamine oxidase dual inhibitor.

  DOI：

  10.1021/jm501501a

文献信息

• Acetylenic and allenic derivatives of 2-(5-benzyloxyindolyl) and 2-(5-hydroxyindolyl)methylamines: synthesis and in vitro evaluation as monoamine oxidase inhibitors
  作者：MA Cruces、C Elorriaga、E Fernandez-Alvarez

  DOI：10.1016/0223-5234(91)90210-e

  日期：1991.1

  We report the synthesis and in vitro studies as MAO inhibitors of 2 series of new acetylenic and allenic derivatives of 2-(5-benzyloxyindolyl)- and 2-(5-hydroxyindolyl)methylamines and their indolylmethylamine precursors. All compounds were MAO inhibitors and either did not show selectivity (the benzyloxy compounds 5) or were selective for MAO-A (most of the hydroxy compounds 7). Three of the studied compounds, 7d, 7g and 7i, were found to be slightly more selective for MAO-A than clorgyline.