4-bromo-N-methyl-N-(4-(6-(methylamino)pyrimidin-4-yl)thiazol-2-yl)benzamide | 1482497-86-8

• 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-bromo-N-methyl-N-(4-(6-(methylamino)pyrimidin-4-yl)thiazol-2-yl)benzamide
• 英文别名: 4-bromo-N-methyl-N-[4-[6-(methylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]benzamide
• CAS: 1482497-86-8
• 化学式: C₁₆H₁₄BrN₅OS
• 分子量: 404.29
• InChiKey: URVJNXUPHFHCTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-bromo-N-methyl-N-(4-(6-(methylamino)pyrimidin-4-yl)thiazol-2-yl)benzamide 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 103.0h， 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
• 作为产物：
  描述：

  4-(6-氯嘧啶-4-基)-n-甲基噻唑-2-胺 在 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 甲苯 为溶剂， 反应 5.0h， 生成 4-bromo-N-methyl-N-(4-(6-(methylamino)pyrimidin-4-yl)thiazol-2-yl)benzamide
  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

文献信息

• J. Med. Chem. 2013, 56, 9146-9155
  作者：

  DOI：——

  日期：——
• Synthesis and Evaluation in Monkey of [¹⁸F]4-Fluoro-<i>N</i>-methyl-<i>N</i>-(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)
  作者：Rong Xu、Paolo Zanotti-Fregonara、Sami S. Zoghbi、Robert L. Gladding、Alicia E. Woock、Robert B. Innis、Victor W Pike

  DOI：10.1021/jm4012017

  日期：2013.11.27

  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.