4-(6-iodoquinoxalin-2-yl)aniline | 1318778-68-5

• 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: 4-(6-iodoquinoxalin-2-yl)aniline
• CAS: 1318778-68-5
• 化学式: C₁₄H₁₀IN₃
• 分子量: 347.158
• InChiKey: FUHRSLGCUKVVGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(6-iodoquinoxalin-2-yl)aniline 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以21.2%的产率得到4-(6-iodoquinoxalin-2-yl)-N-methylaniline
  参考文献：
  名称：

  Novel quinoxaline derivatives for in vivo imaging of β-amyloid plaques in the brain

  摘要：

  In a search for new probes to detect beta-amyloid plaques in the brain of patients with Alzheimer's disease (AD), we have synthesized and evaluated a series of quinoxaline derivatives containing a '6+6-6' ring system. These quinoxaline derivatives showed excellent affinity for A beta(1) (42) aggregates with K(i) values ranging from 2.6 to 10.7 nM. Autoradiography with sections of brain tissue from an animal model of AD mice (APP/PS1) and AD patients revealed that [(125)I]5 labeled beta-amyloid plaques specifically. In biodistribution experiments using normal mice, [(125)I]5 displayed high uptake (6.03% ID/g at 2 min) into and a moderately fast washout from the brain. Although additional refinements are needed to decrease the lipophilicity and improve the washout rate, the quinoxaline scaffold may be useful as a backbone structure to develop novel beta-amyloid imaging agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.079
• 作为产物：
  描述：

  4-碘-2-硝基苯胺 在 盐酸 、 tin(ll) chloride 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 4-(6-iodoquinoxalin-2-yl)aniline
  参考文献：
  名称：

  Novel quinoxaline derivatives for in vivo imaging of β-amyloid plaques in the brain

  摘要：

  In a search for new probes to detect beta-amyloid plaques in the brain of patients with Alzheimer's disease (AD), we have synthesized and evaluated a series of quinoxaline derivatives containing a '6+6-6' ring system. These quinoxaline derivatives showed excellent affinity for A beta(1) (42) aggregates with K(i) values ranging from 2.6 to 10.7 nM. Autoradiography with sections of brain tissue from an animal model of AD mice (APP/PS1) and AD patients revealed that [(125)I]5 labeled beta-amyloid plaques specifically. In biodistribution experiments using normal mice, [(125)I]5 displayed high uptake (6.03% ID/g at 2 min) into and a moderately fast washout from the brain. Although additional refinements are needed to decrease the lipophilicity and improve the washout rate, the quinoxaline scaffold may be useful as a backbone structure to develop novel beta-amyloid imaging agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.079

文献信息

• Novel quinoxaline derivatives for in vivo imaging of β-amyloid plaques in the brain
  作者：Mengchao Cui、Masahiro Ono、Hiroyuki Kimura、Boli Liu、Hideo Saji

  DOI：10.1016/j.bmcl.2011.05.079

  日期：2011.7

  In a search for new probes to detect beta-amyloid plaques in the brain of patients with Alzheimer's disease (AD), we have synthesized and evaluated a series of quinoxaline derivatives containing a '6+6-6' ring system. These quinoxaline derivatives showed excellent affinity for A beta(1) (42) aggregates with K(i) values ranging from 2.6 to 10.7 nM. Autoradiography with sections of brain tissue from an animal model of AD mice (APP/PS1) and AD patients revealed that [(125)I]5 labeled beta-amyloid plaques specifically. In biodistribution experiments using normal mice, [(125)I]5 displayed high uptake (6.03% ID/g at 2 min) into and a moderately fast washout from the brain. Although additional refinements are needed to decrease the lipophilicity and improve the washout rate, the quinoxaline scaffold may be useful as a backbone structure to develop novel beta-amyloid imaging agents. (C) 2011 Elsevier Ltd. All rights reserved.