(4-(N-(4-(6-(tert-butoxycarbonyl(methyl)amino)pyrimidin-4-yl)thiazol-2-yl)-N-(methyl)carbamoyl)phenyl)(phenyl)iodonium tosylate | 1482497-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-(N-(4-(6-(tert-butoxycarbonyl(methyl)amino)pyrimidin-4-yl)thiazol-2-yl)-N-(methyl)carbamoyl)phenyl)(phenyl)iodonium tosylate
• 英文别名: 4-Methylbenzenesulfonate;[4-[methyl-[4-[6-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pyrimidin-4-yl]-1,3-thiazol-2-yl]carbamoyl]phenyl]-phenyliodanium
• CAS: 1482497-90-4
• 化学式: C₇H₇O₃S*C₂₇H₂₇IN₅O₃S
• 分子量: 799.71
• InChiKey: DDSAENBVTJVDJZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  48
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  182
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (4-(N-(4-(6-(tert-butoxycarbonyl(methyl)amino)pyrimidin-4-yl)thiazol-2-yl)-N-(methyl)carbamoyl)phenyl)(phenyl)iodonium tosylate 在 2,2,6,6-四甲基哌啶氧化物 作用下， 以 二甲基亚砜 为溶剂， 生成 Fimx f-18
  参考文献：
  名称：

  Synthesis and Evaluation in Monkey of [¹⁸F]4-Fluoro-N-methyl-N-(4-(6-(methylamino)pyrimidin-4-yl)thiazol-2-yl)benzamide ([¹⁸F]FIMX): A Promising Radioligand for PET Imaging of Brain Metabotropic Glutamate Receptor 1 (mGluR1)

  摘要：

  We sought to develop a PET radioligand that would be useful for imaging human brain metabotropic subtype 1 receptors (mGluR1) in neuropsychiatric disorders and in drug development. 4-Fluoro-N-methyl-N-(4-(6(methylamino)pyrimidin-4-yOthiazol-2-ylbenzamide (FIMX, 11) was identified as having favorable properties for development as a PET radioligand. We developed a method for preparing [F-18]11 in useful radiochemical yield and in high specific activity from [18F]fluoride ion and an N-Boc-protected (phenyl)aryliodonium salt precursor (15). In baseline experiments in rhesus monkey, [F-18 ]11 gave high brain radioactivity uptake, reflecting the expected distribution of mGluR1 with notably high uptake in cerebellum, which became 47% lower by 120 min after radioligand injection. Pharmacological challenges demonstrated that a very high proportion of the radioactivity in monkey brain was bound specifically and reversibly to mGluRl. [F-18]11 is concluded to be an effective PET radioligand for imaging mGluR1 in monkey brain and therefore merits further evaluation in human subjects.

  DOI：

  10.1021/jm4012017
• 作为产物：
  描述：

  4-溴苯甲酰氯 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 108.0h， 生成 (4-(N-(4-(6-(tert-butoxycarbonyl(methyl)amino)pyrimidin-4-yl)thiazol-2-yl)-N-(methyl)carbamoyl)phenyl)(phenyl)iodonium tosylate
  参考文献：
  名称：

  Synthesis and Evaluation in Monkey of [¹⁸F]4-Fluoro-N-methyl-N-(4-(6-(methylamino)pyrimidin-4-yl)thiazol-2-yl)benzamide ([¹⁸F]FIMX): A Promising Radioligand for PET Imaging of Brain Metabotropic Glutamate Receptor 1 (mGluR1)

  摘要：

  We sought to develop a PET radioligand that would be useful for imaging human brain metabotropic subtype 1 receptors (mGluR1) in neuropsychiatric disorders and in drug development. 4-Fluoro-N-methyl-N-(4-(6(methylamino)pyrimidin-4-yOthiazol-2-ylbenzamide (FIMX, 11) was identified as having favorable properties for development as a PET radioligand. We developed a method for preparing [F-18]11 in useful radiochemical yield and in high specific activity from [18F]fluoride ion and an N-Boc-protected (phenyl)aryliodonium salt precursor (15). In baseline experiments in rhesus monkey, [F-18 ]11 gave high brain radioactivity uptake, reflecting the expected distribution of mGluR1 with notably high uptake in cerebellum, which became 47% lower by 120 min after radioligand injection. Pharmacological challenges demonstrated that a very high proportion of the radioactivity in monkey brain was bound specifically and reversibly to mGluRl. [F-18]11 is concluded to be an effective PET radioligand for imaging mGluR1 in monkey brain and therefore merits further evaluation in human subjects.

  DOI：

  10.1021/jm4012017