N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyano-5-fluorophenyl)butan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide | 947371-19-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyano-5-fluorophenyl)butan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide
• CAS: 947371-19-9
• 化学式: C₂₇H₂₄ClF₄N₃O₂
• 分子量: 533.953
• InChiKey: XJYUQAOTWWKWBJ-QMHKHESXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  75
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyano-5-fluorophenyl)butan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide 在 Oxone 、 sodium hydroxide 、 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium acetate 、 碳酸氢钠 、 三环己基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 丙酮 为溶剂， 反应 0.17h， 生成 N-[(1S,2S)-2-(3-cyano-5-fluorophenyl)-3-(4-hydroxyphenyl)-1-methylpropyl]-2-methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide
  参考文献：
  名称：

  Discovery of N-{(1S,2S)-2-(3-Cyanophenyl)- 3-[4-(2-[¹⁸F]fluoroethoxy)phenyl]-1-methylpropyl}- 2-methyl-2-[(5-methylpyridin-2-yl)oxy]propanamide, a Cannabinoid-1 Receptor Positron Emission Tomography Tracer Suitable for Clinical Use

  摘要：

  The discovery of a structurally distinct cannabinoid-1 receptor (CB1R) positron emission tomography tracer is described. Starting from an acyclic amide CB1R inverse agonist (1) as the lead compound, an efficient route to introduce F-18 to the molecule was developed. Further optimization focused on reducing the lipophilicity and increasing the CB1R affinity. These efforts led to the identification of [F-18]-16 that exhibited good brain uptake and an excellent signal-to-noise ratio in rhesus monkeys.

  DOI：

  10.1021/jm070131b
• 作为产物：
  描述：

  在 platinum(IV) oxide N-甲基吗啉 、 盐酸 、 sodium azide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyano-5-fluorophenyl)butan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide
  参考文献：
  名称：

  Discovery of N-{(1S,2S)-2-(3-Cyanophenyl)- 3-[4-(2-[¹⁸F]fluoroethoxy)phenyl]-1-methylpropyl}- 2-methyl-2-[(5-methylpyridin-2-yl)oxy]propanamide, a Cannabinoid-1 Receptor Positron Emission Tomography Tracer Suitable for Clinical Use

  摘要：

  The discovery of a structurally distinct cannabinoid-1 receptor (CB1R) positron emission tomography tracer is described. Starting from an acyclic amide CB1R inverse agonist (1) as the lead compound, an efficient route to introduce F-18 to the molecule was developed. Further optimization focused on reducing the lipophilicity and increasing the CB1R affinity. These efforts led to the identification of [F-18]-16 that exhibited good brain uptake and an excellent signal-to-noise ratio in rhesus monkeys.

  DOI：

  10.1021/jm070131b