N-ethyl-2-[(2-methylphenyl)sulfonyl-(6-oxo-1H-pyridin-3-yl)amino]-N-(pyridin-3-ylmethyl)acetamide | 1435913-07-7

• 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-ethyl-2-[(2-methylphenyl)sulfonyl-(6-oxo-1H-pyridin-3-yl)amino]-N-(pyridin-3-ylmethyl)acetamide
• CAS: 1435913-07-7
• 化学式: C₂₂H₂₄N₄O₄S
• 分子量: 440.523
• InChiKey: WWWLMIFJGVCTFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [11C]methyl iodide 、 N-ethyl-2-[(2-methylphenyl)sulfonyl-(6-oxo-1H-pyridin-3-yl)amino]-N-(pyridin-3-ylmethyl)acetamide 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.05h， 生成 N-ethyl-2-[(6-(111C)methoxypyridin-3-yl)-(2-methylphenyl)sulfonylamino]-N-(pyridin-3-ylmethyl)acetamide
  参考文献：
  名称：

  Radiosynthesis and evaluation of [11C]EMPA as a potential PET tracer for orexin 2 receptors

  摘要：

  EMPA is a selective antagonist of orexin 2 (OX2) receptors. Previous literature with [H-3]-EMPA suggest that it may be used as an imaging agent for OX2 receptors; however, brain penetration is known to be modest. To evaluate the potential of EMPA as a PET radiotracer in non-human primate (as a step to imaging in man), we radiolabeled EMPA with carbon-11. Radiosynthesis of [C-11] N-ethyl-2-(N-(6-methoxypyridin- 3-yl)-2-methylphenylsulfonamido)-N-(pyridin-3-ylmethyl) acetamide ([C-11] EMPA), and evaluation as a potential PET tracer for OX2 receptors is described. Synthesis of an appropriate non-radioactive O-desmethyl precursor was achieved from EMPA with sodium iodide and chlorotrimethylsilane. Selective O-methylation using [C-11] CH3I in the presence of cesium carbonate in DMSO at room temp afforded [C-11] EMPA in 1.5-2.5% yield (non-decay corrected relative to trapped [C-11] CH3I at EOS) with >= 95% chemical and radiochemical purities. The total synthesis time was 34-36 min from EOB. Studies in rodent suggested that uptake in tissue was dominated by nonspecific binding. However, [C-11] EMPA also showed poor uptake in both rats and baboon as measured with PET imaging. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.079
• 作为产物：
  描述：

  邻甲苯磺酰氯 在 吡啶 、 三甲基氯硅烷 、 potassium tert-butylate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium iodide 作用下， 以 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 4.0h， 生成 N-ethyl-2-[(2-methylphenyl)sulfonyl-(6-oxo-1H-pyridin-3-yl)amino]-N-(pyridin-3-ylmethyl)acetamide
  参考文献：
  名称：

  Radiosynthesis and evaluation of [11C]EMPA as a potential PET tracer for orexin 2 receptors

  摘要：

  EMPA is a selective antagonist of orexin 2 (OX2) receptors. Previous literature with [H-3]-EMPA suggest that it may be used as an imaging agent for OX2 receptors; however, brain penetration is known to be modest. To evaluate the potential of EMPA as a PET radiotracer in non-human primate (as a step to imaging in man), we radiolabeled EMPA with carbon-11. Radiosynthesis of [C-11] N-ethyl-2-(N-(6-methoxypyridin- 3-yl)-2-methylphenylsulfonamido)-N-(pyridin-3-ylmethyl) acetamide ([C-11] EMPA), and evaluation as a potential PET tracer for OX2 receptors is described. Synthesis of an appropriate non-radioactive O-desmethyl precursor was achieved from EMPA with sodium iodide and chlorotrimethylsilane. Selective O-methylation using [C-11] CH3I in the presence of cesium carbonate in DMSO at room temp afforded [C-11] EMPA in 1.5-2.5% yield (non-decay corrected relative to trapped [C-11] CH3I at EOS) with >= 95% chemical and radiochemical purities. The total synthesis time was 34-36 min from EOB. Studies in rodent suggested that uptake in tissue was dominated by nonspecific binding. However, [C-11] EMPA also showed poor uptake in both rats and baboon as measured with PET imaging. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.079

文献信息

• Radiosynthesis and evaluation of [11C]EMPA as a potential PET tracer for orexin 2 receptors
  作者：Changning Wang、Christian K. Moseley、Stephen M. Carlin、Colin M. Wilson、Ramesh Neelamegam、Jacob M. Hooker

  DOI：10.1016/j.bmcl.2013.03.079

  日期：2013.6

  EMPA is a selective antagonist of orexin 2 (OX2) receptors. Previous literature with [H-3]-EMPA suggest that it may be used as an imaging agent for OX2 receptors; however, brain penetration is known to be modest. To evaluate the potential of EMPA as a PET radiotracer in non-human primate (as a step to imaging in man), we radiolabeled EMPA with carbon-11. Radiosynthesis of [C-11] N-ethyl-2-(N-(6-methoxypyridin- 3-yl)-2-methylphenylsulfonamido)-N-(pyridin-3-ylmethyl) acetamide ([C-11] EMPA), and evaluation as a potential PET tracer for OX2 receptors is described. Synthesis of an appropriate non-radioactive O-desmethyl precursor was achieved from EMPA with sodium iodide and chlorotrimethylsilane. Selective O-methylation using [C-11] CH3I in the presence of cesium carbonate in DMSO at room temp afforded [C-11] EMPA in 1.5-2.5% yield (non-decay corrected relative to trapped [C-11] CH3I at EOS) with >= 95% chemical and radiochemical purities. The total synthesis time was 34-36 min from EOB. Studies in rodent suggested that uptake in tissue was dominated by nonspecific binding. However, [C-11] EMPA also showed poor uptake in both rats and baboon as measured with PET imaging. (C) 2013 Elsevier Ltd. All rights reserved.