2-(2-hydroxy-3-(1H-indol-1-yl)propylthio)phenol | 1388758-90-4

• 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: 2-(2-hydroxy-3-(1H-indol-1-yl)propylthio)phenol
• 英文别名: 2-(2-Hydroxy-3-indol-1-ylpropyl)sulfanylphenol
• CAS: 1388758-90-4
• 化学式: C₁₇H₁₇NO₂S
• 分子量: 299.393
• InChiKey: JEUANPGDLOBEBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 在 tetrapropylammonium iodide 、 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 2-(2-hydroxy-3-(1H-indol-1-yl)propylthio)phenol
  参考文献：
  名称：

  Synthesis and structure–activity relationship studies of 1,3-disubstituted 2-propanols as BACE-1 inhibitors

  摘要：

  A library of 1,3-disubstituted 2-propanols was synthesized and evaluated as low molecular weight probes for beta-secretase inhibition. By screening a library of 121 1,3-disubstituted 2-propanol derivatives, we identified few compounds inhibiting the enzyme at low micromolar concentrations. The initial hits were optimized to yield a potent BACE-1 inhibitor exhibiting an IC50 constant in the nanomolar range. Exploration of the pharmacological properties revealed that these small molecular inhibitors possessed a high selectivity over cathepsin D and desirable physicochemical properties beneficial to cross the blood-brain barrier. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.072

文献信息

• Synthesis and structure–activity relationship studies of 1,3-disubstituted 2-propanols as BACE-1 inhibitors
  作者：Arun Babu Kumar、Jordan Micheal Anderson、Anthony Lester Melendez、Roman Manetsch

  DOI：10.1016/j.bmcl.2012.05.072

  日期：2012.7

  A library of 1,3-disubstituted 2-propanols was synthesized and evaluated as low molecular weight probes for beta-secretase inhibition. By screening a library of 121 1,3-disubstituted 2-propanol derivatives, we identified few compounds inhibiting the enzyme at low micromolar concentrations. The initial hits were optimized to yield a potent BACE-1 inhibitor exhibiting an IC50 constant in the nanomolar range. Exploration of the pharmacological properties revealed that these small molecular inhibitors possessed a high selectivity over cathepsin D and desirable physicochemical properties beneficial to cross the blood-brain barrier. (C) 2012 Elsevier Ltd. All rights reserved.