2-(4-(2-fluoroethoxy)phenyl)-N-methylquinoxalin-6-amine | 1415328-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(4-(2-fluoroethoxy)phenyl)-N-methylquinoxalin-6-amine
• 英文别名: 2-[4-(2-fluoroethoxy)phenyl]-N-methylquinoxalin-6-amine
• CAS: 1415328-12-9
• 化学式: C₁₇H₁₆FN₃O
• 分子量: 297.332
• InChiKey: OWZPFCUDLPYIPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 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：
  47
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(6-aminoquinoxalin-2-yl)phenol 在 sodium tetrahydroborate 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-(4-(2-fluoroethoxy)phenyl)-N-methylquinoxalin-6-amine
  参考文献：
  名称：

  18F-Labeled 2-phenylquinoxaline derivatives as potential positron emission tomography probes for in vivo imaging of β-amyloid plaques

  摘要：

  In continuation of our study on the 2-phenylquinoxaline scaffold as potential beta-amyloid imaging probes, two [F-18]fluoro-pegylated 2-phenylquinoxaline derivatives, 2-(4-(2-[F-18]fluoroethoxy)phenyl)-N-methylquinoxalin-6-amine ([F-18]4a) and 2-(4-(2-(2-(2-[F-18]fluoroethoxy)ethoxy)ethoxy)phenyl)-N-methylquinoxalin-6-amine ([F-18]4b) were prepared. Both of them displayed high binding affinity to A beta(1-42) aggregates (K-i = 10.0 +/- 1.4 nM for 4a, K-i = 5.3 +/- 3.2 nM for 4b). The specific and high binding of [F-18]4a and [F-18]4b to A beta plaques was confirmed by in vitro autoradiography on brain sections of AD human and transgenic mice. In biodistribution in normal mice, [F-18]4a displayed high initial brain uptake (8.17% ID/g at 2 min) and rapid washout from the brain. These preliminary results suggest [F-18]4a may be a potential PET imaging agent for AI plaques in the living human brain. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.031

文献信息

• 18F-Labeled 2-phenylquinoxaline derivatives as potential positron emission tomography probes for in vivo imaging of β-amyloid plaques
  作者：Pingrong Yu、Mengchao Cui、Xuedan Wang、Xiaojun Zhang、Zijing Li、Yanping Yang、Jianhua Jia、Jinming Zhang、Masahiro Ono、Hideo Saji、Hongmei Jia、Boli Liu

  DOI：10.1016/j.ejmech.2012.08.031

  日期：2012.11

  In continuation of our study on the 2-phenylquinoxaline scaffold as potential beta-amyloid imaging probes, two [F-18]fluoro-pegylated 2-phenylquinoxaline derivatives, 2-(4-(2-[F-18]fluoroethoxy)phenyl)-N-methylquinoxalin-6-amine ([F-18]4a) and 2-(4-(2-(2-(2-[F-18]fluoroethoxy)ethoxy)ethoxy)phenyl)-N-methylquinoxalin-6-amine ([F-18]4b) were prepared. Both of them displayed high binding affinity to A beta(1-42) aggregates (K-i = 10.0 +/- 1.4 nM for 4a, K-i = 5.3 +/- 3.2 nM for 4b). The specific and high binding of [F-18]4a and [F-18]4b to A beta plaques was confirmed by in vitro autoradiography on brain sections of AD human and transgenic mice. In biodistribution in normal mice, [F-18]4a displayed high initial brain uptake (8.17% ID/g at 2 min) and rapid washout from the brain. These preliminary results suggest [F-18]4a may be a potential PET imaging agent for AI plaques in the living human brain. (C) 2012 Elsevier Masson SAS. All rights reserved.