4-(1H-indol-2-yl)-N-methylbenzenenamine | 1252037-82-3

• 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: 4-(1H-indol-2-yl)-N-methylbenzenenamine
• 英文别名: [4-(1H-indol-2-yl)phenyl](methyl)amine；4-(1H-indol-2-yl)-N-methylaniline
• CAS: 1252037-82-3
• 化学式: C₁₅H₁₄N₂
• 分子量: 222.29
• InChiKey: ZPVYIKFQFHGDFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(1H-indol-2-yl)-N-methylbenzenenamine 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 potassium n-butoxide 、 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 、 potassium iodide 、 氢氟酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 78.25h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of 18F-labled 2-phenylindole derivatives as PET imaging probes for β-amyloid plaques

  摘要：

  A novel series of fluorinated 2-phenylindole derivatives were synthesized and evaluated as beta-amyloid imaging probes for PET. The in vitro inhibition assay demonstrated that their binding affinities for A beta(1-42) aggregates ranged from 28.4 to 1097.8 nM. One ligand was labeled with F-18 ([F-18]1a) for its high affinity (K-i = 28.4 nM), which was also confirmed by in vitro autoradiography experiments on brain sections of transgenic mouse (C57BL6, APPswe/PSEN1, 11 months old, male). In vivo biodistribution experiments in normal mice showed that this radiotracer displayed high initial uptake (5.82 +/- 0.51% ID/g at 2 min) into and moderate washout (2.77 +/- 0.31% ID/g at 60 min) from the brain. [F-18]1a could be developed as a promising new PET imaging probe for A beta plaques although necessary modifications are still needed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.028
• 作为产物：
  描述：

  4-氨基苯乙酮 、 1-甲基-1-苯肼 在 polyphosphoric acid 作用下， 反应 3.0h， 以47%的产率得到4-(1H-indol-2-yl)-N-methylbenzenenamine
  参考文献：
  名称：

  Synthesis and biological evaluation of 18F-labled 2-phenylindole derivatives as PET imaging probes for β-amyloid plaques

  摘要：

  A novel series of fluorinated 2-phenylindole derivatives were synthesized and evaluated as beta-amyloid imaging probes for PET. The in vitro inhibition assay demonstrated that their binding affinities for A beta(1-42) aggregates ranged from 28.4 to 1097.8 nM. One ligand was labeled with F-18 ([F-18]1a) for its high affinity (K-i = 28.4 nM), which was also confirmed by in vitro autoradiography experiments on brain sections of transgenic mouse (C57BL6, APPswe/PSEN1, 11 months old, male). In vivo biodistribution experiments in normal mice showed that this radiotracer displayed high initial uptake (5.82 +/- 0.51% ID/g at 2 min) into and moderate washout (2.77 +/- 0.31% ID/g at 60 min) from the brain. [F-18]1a could be developed as a promising new PET imaging probe for A beta plaques although necessary modifications are still needed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.028

文献信息

• Novel Indole Derivatives as Potential Imaging Agents for Alzheimer's Disease
  作者：Lihai Yu、Matthias Scheunemann、Winnie Deuther-Conrad、Achim Hiller、Steffen Fischer、Dietlind Sorger、Osama Sabri、Hongmei Jia、Jorg Steinbach、Peter Brust、Boli Liu

  DOI：10.5012/bkcs.2010.31.01.177

  日期：2010.1.20