[18F]-5-((4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)ethynyl)-1H-indole | 1073191-34-0

• 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: [18F]-5-((4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)ethynyl)-1H-indole
• 英文别名: 5-[2-[4-[2-[2-(2-(18F)fluoranylethoxy)ethoxy]ethoxy]phenyl]ethynyl]-1H-indole
• CAS: 1073191-34-0
• 化学式: C₂₂H₂₂FNO₃
• 分子量: 366.422
• InChiKey: MSJMCPCMWUJNMH-VNRZBHCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(2-(2-(4-((1H-indol-5-yl)ethynyl)phenoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate 在 potassium [¹⁸F]fluoride 、 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 二甲基亚砜 为溶剂， 反应 0.07h， 生成 [18F]-5-((4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)ethynyl)-1H-indole
  参考文献：
  名称：

  Synthesis and evaluation of indolinyl- and indolylphenylacetylenes as PET imaging agents for β-amyloid plaques

  摘要：

  Two new phenylacetylene derivatives, 5-((4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)ethynyl)indoline 8 and 5-((4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)ethynyl)-1H-indole 14, targeting beta-amyloid ( Ab) plaques have been prepared. In vitro binding carried out in tissue homogenates prepared from postmortem AD brains with [(125)[] IMPY (6-iodo-2-(40-dimethylamino-phenyl-imidazo[1,2-a]pyridine) as the radioligand indicated good binding affinities (K-i = 4.0 and 1.5 nM for 8 and 14, respectively). Brain penetration of the corresponding radiofluorinated ligands, evaluated in the normal mice, showed good initial brain penetration (4.50 and 2.43% ID/g (injected dose/gram) for [F-18]8 and [F-18]14 at 2 min after injection) with moderate to low washout rates from the brain (1.71% ID/g at 2h and 2.10% ID/g at 3 h, respectively). Autoradiography and homogenate binding studies demonstrated the high specific binding of [F-18]14 to the Ab plaques; however, [F-18]8 showed low specific binding. These preliminary results identified that indolylphenylacetylene, 14, may be a good lead for further structural modi. cation to develop a useful Ab plaque imaging agent. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.077

文献信息

• Synthesis and evaluation of indolinyl- and indolylphenylacetylenes as PET imaging agents for β-amyloid plaques
  作者：Wenchao Qu、Seok-Rye Choi、Catherine Hou、Zhiping Zhuang、Shunichi Oya、Wei Zhang、Mei-Ping Kung、Rajesh Manchandra、Daniel M. Skovronsky、Hank F. Kung

  DOI：10.1016/j.bmcl.2008.07.077

  日期：2008.9

  Two new phenylacetylene derivatives, 5-((4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)ethynyl)indoline 8 and 5-((4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)ethynyl)-1H-indole 14, targeting beta-amyloid ( Ab) plaques have been prepared. In vitro binding carried out in tissue homogenates prepared from postmortem AD brains with [(125)[] IMPY (6-iodo-2-(40-dimethylamino-phenyl-imidazo[1,2-a]pyridine) as the radioligand indicated good binding affinities (K-i = 4.0 and 1.5 nM for 8 and 14, respectively). Brain penetration of the corresponding radiofluorinated ligands, evaluated in the normal mice, showed good initial brain penetration (4.50 and 2.43% ID/g (injected dose/gram) for [F-18]8 and [F-18]14 at 2 min after injection) with moderate to low washout rates from the brain (1.71% ID/g at 2h and 2.10% ID/g at 3 h, respectively). Autoradiography and homogenate binding studies demonstrated the high specific binding of [F-18]14 to the Ab plaques; however, [F-18]8 showed low specific binding. These preliminary results identified that indolylphenylacetylene, 14, may be a good lead for further structural modi. cation to develop a useful Ab plaque imaging agent. (C) 2008 Elsevier Ltd. All rights reserved.