4-(piperidin-1-ylmethyl)phenyl-1H-indole-3-carboxylate | 1234202-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(piperidin-1-ylmethyl)phenyl-1H-indole-3-carboxylate
• 英文别名: [4-(piperidin-1-ylmethyl)phenyl] 1H-indole-3-carboxylate
• CAS: 1234202-20-0
• 化学式: C₂₁H₂₂N₂O₂
• 分子量: 334.418
• InChiKey: FMEBLCVXTAPZLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-吲哚甲酸 、 4-(哌啶-1-基甲基)苯酚 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以27.1%的产率得到4-(piperidin-1-ylmethyl)phenyl-1H-indole-3-carboxylate
  参考文献：
  名称：

  Design and synthesis of novel 3-substituted-indole derivatives as selective H3 receptor antagonists and potent free radical scavengers

  摘要：

  A series of novel 3-substituted-indole derivatives with a benzyl tertiary amino moiety were designed, synthesized and evaluated as H-3 receptor antagonists and free radical scavengers for Alzheimer's disease therapy. Most of these synthesized compounds exhibited moderate to potent antagonistic activities in CREs driven luciferase assay. In particular, compound 2d demonstrated the most favorable H-3 receptor antagonistic activity with the IC50 value of 0.049 mu M. Besides, it also displayed high binding affinity to H-3 receptor (K-i = 4.26 +/- 2.55 nM) and high selectivity over other three histamine receptors. Moreover, 2d and other two 3-substituted indole derivatives 1d and 3d exerted potent ABTS radical cation scavenging capacities similar to melatonin. Above results illustrate that 2d is an interesting lead for extensive optimization to explore new drug candidate for AD therapy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.051

文献信息

• Design and synthesis of novel 3-substituted-indole derivatives as selective H3 receptor antagonists and potent free radical scavengers
  作者：Li Tang、Liying Zhao、Lingjuan Hong、Fenyan Yang、Rong Sheng、Jianzhong Chen、Ying Shi、Naimin Zhou、Yongzhou Hu

  DOI：10.1016/j.bmc.2013.07.051

  日期：2013.10

  A series of novel 3-substituted-indole derivatives with a benzyl tertiary amino moiety were designed, synthesized and evaluated as H-3 receptor antagonists and free radical scavengers for Alzheimer's disease therapy. Most of these synthesized compounds exhibited moderate to potent antagonistic activities in CREs driven luciferase assay. In particular, compound 2d demonstrated the most favorable H-3 receptor antagonistic activity with the IC50 value of 0.049 mu M. Besides, it also displayed high binding affinity to H-3 receptor (K-i = 4.26 +/- 2.55 nM) and high selectivity over other three histamine receptors. Moreover, 2d and other two 3-substituted indole derivatives 1d and 3d exerted potent ABTS radical cation scavenging capacities similar to melatonin. Above results illustrate that 2d is an interesting lead for extensive optimization to explore new drug candidate for AD therapy. (C) 2013 Elsevier Ltd. All rights reserved.