4-(6-Methylsulfanylimidazo[1,2-a]pyridin-2-yl)aniline | 1005417-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(6-Methylsulfanylimidazo[1,2-a]pyridin-2-yl)aniline
• CAS: 1005417-06-0
• 化学式: C₁₄H₁₃N₃S
• 分子量: 255.343
• InChiKey: AEDCJFPKFVWIEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 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：
  68.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(6-iodo-H-imidazo[1,2-a]pyridin-2-yl)benzenamine 、 sodium thiomethoxide 在 tris(dibenzylideneacetone)dipalladium (0) 、 1,1'-bis(diisopropylphosphino)ferrocene SnCl(CH₃)3 作用下， 以 四氢呋喃 为溶剂， 110.0 ℃ 、1.72 MPa 条件下， 反应 0.17h， 以26%的产率得到4-(6-Methylsulfanylimidazo[1,2-a]pyridin-2-yl)aniline
  参考文献：
  名称：

  Synthesis and Evaluation of N-Methyl and S-Methyl ¹¹C-Labeled 6-Methylthio-2-(4′-N,N-dimethylamino)phenylimidazo[1,2-a]pyridines as Radioligands for Imaging β-Amyloid Plaques in Alzheimer’s Disease

  摘要：

  6-Thiolato-substituted 2-(4'-N,N-dimethylamino)phenylimidazo[1,2-a]pyridines (RS-IMPYs; 1-4) were synthesized as candidates for labeling with carbon-11 (t(1/2) = 20.4 min) and imaging of A(beta) plaques in living human brain using positron emission tomography (PET). K-i values for binding of these ligands to Alzheimer's disease brain homogenates were measured in vitro,against tritium-labeled 6 (Pittsburgh compound B). MeS-IMPY (3, K-i = 7.93 nM) was labeled with carbon-11 at its S- or N-methyl position to give [C-11]7 or [C-11]8, respectively. After injection into rats, [C-11]7 or [C-11]8 gave moderately high brain uptakes of radioactivity followed by rapid washout to low levels. The ratio of radioactivity at maximal uptake to that at 60 min reached 18.7 for [C-11]7. [C-11]7 behaved similarly in mouse and monkey. [C-11]7 also bound selectively to A(beta) plaques in post mortem human Alzheimer's disease brain. Although rapidly metabolized in rat by N-demethylation, [C-11]7 was stable in rat brain homogenates. The ex vivo brain radiometabolites observed in rats have a peripheral origin. Overall, [C-11]7 merits further evaluation in human subjects.

  DOI：

  10.1021/jm700970s

文献信息

• Synthesis and Evaluation of <i>N</i>-Methyl and <i>S</i>-Methyl ¹¹C-Labeled 6-Methylthio-2-(4′-<i>N</i>,<i>N</i>-dimethylamino)phenylimidazo[1,2-<i>a</i>]pyridines as Radioligands for Imaging β-Amyloid Plaques in Alzheimer’s Disease
  作者：Lisheng Cai、Jeih-San Liow、Sami S. Zoghbi、Jessica Cuevas、Cesar Baetas、Jinsoo Hong、H. Umesha Shetty、Nicholas M. Seneca、Amira K. Brown、Robert Gladding、Sebastian S. Temme、Mary M. Herman、Robert B. Innis、Victor W. Pike

  DOI：10.1021/jm700970s

  日期：2008.1.1

  6-Thiolato-substituted 2-(4'-N,N-dimethylamino)phenylimidazo[1,2-a]pyridines (RS-IMPYs; 1-4) were synthesized as candidates for labeling with carbon-11 (t(1/2) = 20.4 min) and imaging of A(beta) plaques in living human brain using positron emission tomography (PET). K-i values for binding of these ligands to Alzheimer's disease brain homogenates were measured in vitro,against tritium-labeled 6 (Pittsburgh compound B). MeS-IMPY (3, K-i = 7.93 nM) was labeled with carbon-11 at its S- or N-methyl position to give [C-11]7 or [C-11]8, respectively. After injection into rats, [C-11]7 or [C-11]8 gave moderately high brain uptakes of radioactivity followed by rapid washout to low levels. The ratio of radioactivity at maximal uptake to that at 60 min reached 18.7 for [C-11]7. [C-11]7 behaved similarly in mouse and monkey. [C-11]7 also bound selectively to A(beta) plaques in post mortem human Alzheimer's disease brain. Although rapidly metabolized in rat by N-demethylation, [C-11]7 was stable in rat brain homogenates. The ex vivo brain radiometabolites observed in rats have a peripheral origin. Overall, [C-11]7 merits further evaluation in human subjects.