[O-methyl-(11)C]WAY-100635 | 158238-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: [O-methyl-(11)C]WAY-100635
• 英文别名: 3Yqy8P5qgx；N-[2-[4-(2-(111C)methoxyphenyl)piperazin-1-yl]ethyl]-N-pyridin-2-ylcyclohexanecarboxamide
• CAS: 158238-18-7
• 化学式: C₂₅H₃₄N₄O₂
• 分子量: 421.56
• InChiKey: SBPRIAGPYFYCRT-BJUDXGSMSA-N

物化性质

• 密度：
  1.154±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  48.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  [11C]methyl triflate 、 Desmethyl-WAY-100635 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 生成 [O-methyl-(11)C]WAY-100635
  参考文献：
  名称：

  Improved syntheses of the PET radioligands, [11C]FLB 457, [11C]MDL 100907 and [11C]β-CIT-FE, by the use of [11C]methyl triflate

  摘要：

  The highly reactive labelling agent,[C-11]methyl triflate, was used to synthesise three recently developed PET radioligands. The labelling reactions were C-11-methylations of phenols for the preparations of the D-2 receptor radioligand, [C-11]FLB 457, and the 5-MT2A receptor radioligand, [C-11]MDL 100907, and C-11-methylation of a carboxylic acid for the preparation of the dopamine transporter radioligand, [C-11]beta-CIT-FE. The synthesis of the 5-MT1A receptor radioligand, [O-methyl-C-11]WAY-100635, was used to establish general reaction conditions for the methylation of phenols with [C-11]methyl triflate. Compared to the previous use of [C-11]methyl iodide in these radiosyntheses, [C-11]methyl triflate demanded less precursor, allowed faster reactions and improved radiochemical yields. Normal-phase HPLC was used to speed up product purifications (except for [C-11]beta-CIT-FE). Hence, preparation times were shorter, resulting in radioligands with higher specific radioactivity.

  DOI：

  10.1002/(sici)1099-1344(199806)41:6<545::aid-jlcr99>3.0.co;2-7

文献信息

• Pike, Victor W.; McCarron, Julie A.; Hume, Susan P., Medicinal Chemistry Research, 1995, vol. 5, # 2/3, p. 208 - 227
  作者：Pike, Victor W.、McCarron, Julie A.、Hume, Susan P.、Ashworth, Sharon、Opacka-Juffry, Jolanta、et al.

  DOI：——

  日期：——
• Lundkvist, C.; Sandell, J.; Nagren, K., Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 583 - 585
  作者：Lundkvist, C.、Sandell, J.、Nagren, K.、Pike, V. W.、Swahn, C.-G.、et al.

  DOI：——

  日期：——
• Solid-phase radiosynthesis of [11C]WAY 100635
  作者：Alan A. Wilson、Jean N. DaSilva、Sylvain Houle

  DOI：10.1002/(sici)1099-1344(199602)38:2<149::aid-jlcr824>3.0.co;2-8

  日期：1996.2

  An efficient, fast and simple method is described for the radiosynthesis of the potent and selective 5-HT1A antagonist [O-methyl-C-11]-N-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-N-(2-pyridinyl)cyclohexane carboxamide ([C-11]WAY 100635). [C-11]Iodomethane was effectively trapped on a C-18 reverse-phase cartridge at ambient temperature where it reacted rapidly with the normethyl precursor, N-[2-[4-(2-hydroxyphenyl)-1-piperazinyl]ethyl]-N-(2-pyridinyl) cyclohexane carboxamide. Following high performance liquid chromatography purification and formulation, [C-11]WAY 100635 was obtained in high radiochemical yields (40%, uncorrected from [C-11]Iiodomethane) in a synthesis time of 25 min with an average specific actvity of (at end-of-synthesis) 33 GBq/mu mole (900 mCi/mu mole).