N-[2-(5-ethoxyindol-3-yl)ethyl]thioacetamide | 663955-25-7

• 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: N-[2-(5-ethoxyindol-3-yl)ethyl]thioacetamide
• 英文别名: N-(2-(5-Ethoxy-1H-indol-3-yl)ethyl)ethanethioamide；N-[2-(5-ethoxy-1H-indol-3-yl)ethyl]ethanethioamide
• CAS: 663955-25-7
• 化学式: C₁₄H₁₈N₂OS
• 分子量: 262.376
• InChiKey: ZAYCXZZASINNOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(2-Acetamino-ethyl)-5-ethoxy-indol 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以23%的产率得到N-[2-(5-ethoxyindol-3-yl)ethyl]thioacetamide
  参考文献：
  名称：

  Binding affinity and biological activity of oxygen and sulfur isosteres at melatonin receptors as a function of their hydrogen bonding capability

  摘要：

  Analogues of melatonin (1) and of N-acetyl 5-ethoxytryptamine (3) in which the oxygen atoms are replaced by sulfur have been prepared and tested against human and amphibian melatonin receptors. All sulfur analogues show a decreased binding affinity at human NIT, and MT(2) receptors and a reduced potency as melatonin agonists on the Xenopus melanophore assay. The 5-methoxy oxygen of melatonin is significantly more important for receptor binding than the amide oxygen. N-Acetyl 5-ethoxytryptamine shows a decrease in both binding affinity and potency in comparison with melatonin. In this series, replacing either the ethoxy or amide oxygen by sulfur has a similar but smaller effect on both binding affinity and potency. Using K H values from Abraham's equations we have assessed the possibility of estimating EC(50) values for sulfur isosteres from the EC(50) values of their oxygen analogues. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2003.09.004

文献信息

• Binding affinity and biological activity of oxygen and sulfur isosteres at melatonin receptors as a function of their hydrogen bonding capability
  作者：David J Davies、Rüdiger Faust、Peter J Garratt、Cécile Marivingt-Mounir、Kathryn Davidson、Muy-Teck Teh、David Sugden

  DOI：10.1016/j.bioorg.2003.09.004

  日期：2004.2

  Analogues of melatonin (1) and of N-acetyl 5-ethoxytryptamine (3) in which the oxygen atoms are replaced by sulfur have been prepared and tested against human and amphibian melatonin receptors. All sulfur analogues show a decreased binding affinity at human NIT, and MT(2) receptors and a reduced potency as melatonin agonists on the Xenopus melanophore assay. The 5-methoxy oxygen of melatonin is significantly more important for receptor binding than the amide oxygen. N-Acetyl 5-ethoxytryptamine shows a decrease in both binding affinity and potency in comparison with melatonin. In this series, replacing either the ethoxy or amide oxygen by sulfur has a similar but smaller effect on both binding affinity and potency. Using K H values from Abraham's equations we have assessed the possibility of estimating EC(50) values for sulfur isosteres from the EC(50) values of their oxygen analogues. (C) 2003 Elsevier Inc. All rights reserved.