N-methyl-N-(111C)methyl-4-(6-methylsulfanylimidazo[1,2-a]pyridin-2-yl)aniline | 1005417-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-methyl-N-(111C)methyl-4-(6-methylsulfanylimidazo[1,2-a]pyridin-2-yl)aniline
• CAS: 1005417-11-7
• 化学式: C₁₆H₁₇N₃S
• 分子量: 282.386
• InChiKey: WOYCDVDURLTMAW-BJUDXGSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-methyl-4-(6-methylsulfanylimidazo[1,2-a]pyridin-2-yl)aniline 、 [11C]methyl triflate 以 丁酮 为溶剂， 反应 0.03h， 生成 N-methyl-N-(111C)methyl-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

• Radiolabelling Method Using Cycloalkyl Groups
  申请人：Graham Keith

  公开号：US20120189546A1

  公开（公告）日：2012-07-26

  This invention relates to novel cyclo alkyl compounds suitable for labeling by 18 F, methods of preparing such a compound, compositions comprising such compounds, kits comprising such compounds or compositions and uses of such compounds, compositions or kits for diagnostic imaging by positron emission tomography (PET).

  本发明涉及新型环烷基化合物，适用于18F标记，制备这种化合物的方法，包含这种化合物的组合物，包含这种化合物或组合物的试剂盒以及这种化合物、组合物或试剂盒在正电子发射断层扫描（PET）诊断成像中的用途。
• 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.