3-(2-nitrovinyl)-5-methylthioindole | 663955-29-1

• 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: 3-(2-nitrovinyl)-5-methylthioindole
• 英文别名: 5-methylsulfanyl-3-(2-nitroethenyl)-1H-indole
• CAS: 663955-29-1
• 化学式: C₁₁H₁₀N₂O₂S
• 分子量: 234.279
• InChiKey: VRFXWLXVCBQDCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  58.93
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(2-nitrovinyl)-5-methylthioindole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-[2-(5-methylthioindol-3-yl)ethyl]acetamide
  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
• 作为产物：
  描述：

  5-methylthioindole-3-carboxaldehyde 、 硝基甲烷 在 哌啶 、 溶剂黄146 作用下， 以 苯 为溶剂， 生成 3-(2-nitrovinyl)-5-methylthioindole
  参考文献：
  名称：

  Synthesis and structure–activity relationship of novel conformationally restricted analogues of serotonin as 5-HT₆ receptor ligands

  摘要：

  5-Hydroxytryptamine 6 receptors (5-HT6R) are being perceived as the possible target for treatment of cognitive disorders as well as obesity. The present article deals with the design, synthesis, in vitro binding and structure-activity relationship of a novel series of tetracyclic tryptamines with the rigidized N-arylsulphonyl, N-arylcarbonyl and N-benzyl substituents as 5-HT6 receptor ligands. The chiral sulphonyl derivatives 15a and 17a showed high affinity at 5-HT6R with the K-i of 23.4 and 20.5 nM, respectively. The lead compound from the series 15a has acceptable ADME properties, adequate brain penetration and is active in animal models of cognition like Novel Object Recognition Task (NORT) and water maze.

  DOI：

  10.3109/14756366.2011.595713