MK-9470 | 947371-30-4

• 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: MK-9470
• 英文别名: Propanamide, N-((1S,2S)-2-(3-cyanophenyl)-3-(4-(2-fluoroethoxy)phenyl)-1-methylpropyl)-2-methyl-2-((5-methyl-2-pyridinyl)oxy)-；N-[(2S,3S)-3-(3-cyanophenyl)-4-[4-(2-fluoroethoxy)phenyl]butan-2-yl]-2-methyl-2-(5-methylpyridin-2-yl)oxypropanamide
• CAS: 947371-30-4
• 化学式: C₂₉H₃₂FN₃O₃
• 分子量: 489.59
• InChiKey: XIYPJXKEMLKFMD-HFZDXXHNSA-N

物化性质

• 沸点：
  668.5±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-羟基-5-甲基嘧啶 在 N-甲基吗啉 、 sodium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 caesium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 MK-9470
  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

文献信息

• Substituted amides
  申请人：Burns H. Donald

  公开号：US20060115425A1

  公开（公告）日：2006-06-01

  The present invention relates to particular radiolabeled Cannabinoid-1 (CB1) receptor modulators, and methods of using these modulators for labeling and diagnostic imaging of Cannabinoid-1 receptors in mammals, particularly humans. In addition, intermediates useful for the synthesis of the radiolabeled Cannabinoid-1 receptor modulators are also disclosed, as well as the processes for synthesizing the radiolabeled Cannabinoid-1 receptor modulators. Still further, formulations of the radiolabeled Cannabinoid-1 receptor compounds are described.

  本发明涉及特定的放射性标记的Cannabinoid-1（CB1）受体调节剂，以及使用这些调节剂进行哺乳动物，特别是人类Cannabinoid-1受体的标记和诊断成像的方法。此外，还公开了用于合成放射性标记的Cannabinoid-1受体调节剂的中间体，以及合成放射性标记的Cannabinoid-1受体调节剂的过程。此外，还描述了放射性标记的Cannabinoid-1受体化合物的配方。
• US7754188B2
  申请人：——

  公开号：US7754188B2

  公开（公告）日：2010-07-13
• Discovery of <i>N</i>-{(1<i>S</i>,2<i>S</i>)-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
  作者：Ping Liu、Linus S. Lin、Terence G. Hamill、James P. Jewell、Thomas J. Lanza、Raymond E. Gibson、Stephen M. Krause、Christine Ryan、Waisi Eng、Sandra Sanabria、Xinchun Tong、Junying Wang、Dorothy A. Levorse、Karen A. Owens、Tung M. Fong、Chun-Pyn Shen、Julie Lao、Sanjeev Kumar、Wenji Yin、Joseph F. Payack、Shawn A. Springfield、Richard Hargreaves、H. Donald Burns、Mark T. Goulet、William K. Hagmann

  DOI：10.1021/jm070131b

  日期：2007.7.1

  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.