N-[4-(6-chloropyrimidin-4-yl)-1,3-thiazol-2-yl]-N-methyl-4-(tributylstannyl)benzamide | 1414953-58-4

• 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: N-[4-(6-chloropyrimidin-4-yl)-1,3-thiazol-2-yl]-N-methyl-4-(tributylstannyl)benzamide
• 英文别名: N-[4-(6-chloropyrimidin-4-yl)-1,3-thiazol-2-yl]-N-methyl-4-tributylstannylbenzamide
• CAS: 1414953-58-4
• 化学式: C₂₇H₃₇ClN₄OSSn
• 分子量: 619.846
• InChiKey: MHJRIEJILUIIPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.59
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  87.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[4-(6-chloropyrimidin-4-yl)-1,3-thiazol-2-yl]-N-methyl-4-(tributylstannyl)benzamide 、 异丙胺 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以70.8%的产率得到N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methyl-4-(tributylstannyl)benzamide
  参考文献：
  名称：

  Development of N-[4-[6-(Isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methyl-4-[¹¹C]methylbenzamide for Positron Emission Tomography Imaging of Metabotropic Glutamate 1 Receptor in Monkey Brain

  摘要：

  Three novel 4-substituted benzamides have been synthesized as potential ligands for the positron emission tomography (PET) imaging of metabotropic glutamate 1 (mGlu1) receptor in the brain. Of these compounds, N-(4-(6-(isopropylamino)pyrimidin-4-yl)-1,3-thiazol-2-yl)-N,4-dimethylbenzamide (4) exhibited the highest binding affinity (K-i = 13.6 nM) for mGlu1 and was subsequently labeled with carbon-11. In vitro autoradiography using rat brain sections showed that [C-11]4 binding was consistent with the distribution of mGlu1, with high specific binding in the cerebellum and thalamus. PET studies with [C-11]4 in monkey showed a high brain uptake and a kinetic profile suitable for quantitative analysis. Pretreatment with a mGlu1-selective ligand 16 largely decreased the brain uptake, indicating high in vivo specific binding of [C-11]4 to mGlu1. In metabolite analysis, only unchanged [C-11]4 was found in the brain. [C-11]4 is a useful PET ligand for the imaging and quantitative analysis of mGlu1 in monkey brain and merits further evaluation in humans.

  DOI：

  10.1021/jm301597s
• 作为产物：
  描述：

  六正丁基二锡 在 四(三苯基膦)钯 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 、 lithium chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 37.0h， 生成 N-[4-(6-chloropyrimidin-4-yl)-1,3-thiazol-2-yl]-N-methyl-4-(tributylstannyl)benzamide
  参考文献：
  名称：

  Development of N-[4-[6-(Isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methyl-4-[¹¹C]methylbenzamide for Positron Emission Tomography Imaging of Metabotropic Glutamate 1 Receptor in Monkey Brain

  摘要：

  Three novel 4-substituted benzamides have been synthesized as potential ligands for the positron emission tomography (PET) imaging of metabotropic glutamate 1 (mGlu1) receptor in the brain. Of these compounds, N-(4-(6-(isopropylamino)pyrimidin-4-yl)-1,3-thiazol-2-yl)-N,4-dimethylbenzamide (4) exhibited the highest binding affinity (K-i = 13.6 nM) for mGlu1 and was subsequently labeled with carbon-11. In vitro autoradiography using rat brain sections showed that [C-11]4 binding was consistent with the distribution of mGlu1, with high specific binding in the cerebellum and thalamus. PET studies with [C-11]4 in monkey showed a high brain uptake and a kinetic profile suitable for quantitative analysis. Pretreatment with a mGlu1-selective ligand 16 largely decreased the brain uptake, indicating high in vivo specific binding of [C-11]4 to mGlu1. In metabolite analysis, only unchanged [C-11]4 was found in the brain. [C-11]4 is a useful PET ligand for the imaging and quantitative analysis of mGlu1 in monkey brain and merits further evaluation in humans.

  DOI：

  10.1021/jm301597s