(2S,3S)-N-tert-butoxycarbonyl-2-[α-(2-iodophenylthio)phenylmethyl]morpholine | 1097104-39-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2S,3S)-N-tert-butoxycarbonyl-2-[α-(2-iodophenylthio)phenylmethyl]morpholine
• 英文别名: tert-butyl (2S)-2-[(S)-(2-iodophenyl)sulfanyl-phenylmethyl]morpholine-4-carboxylate
• CAS: 1097104-39-6
• 化学式: C₂₂H₂₆INO₃S
• 分子量: 511.424
• InChiKey: MYVIEZAHAMAJAR-ICSRJNTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S,3R)-N-tert-butoxycarbonyl-2-[α-bromo(phenyl)methyl]morpholine 、 2-碘苯硫酚 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以63%的产率得到(2S,3S)-N-tert-butoxycarbonyl-2-[α-(2-iodophenylthio)phenylmethyl]morpholine
  参考文献：
  名称：

  Synthesis, Radiosynthesis, and Biological Evaluation of Carbon-11 and Fluorine-18 Labeled Reboxetine Analogues: Potential Positron Emission Tomography Radioligands for in Vivo Imaging of the Norepinephrine Transporter

  摘要：

  Reboxetine analogues with methyl and fluoroalkyl substituents at position 2 of the phenoxy ring 1-4 were synthesized. In vitro competition binding with [H-3]nisoxetine demonstrated that 1-4 have a high affinity for the norepinephrine transporter (NET) with K-i's = 1.02, 3.14, 3.68, and 0.30 nM, respectively. MicroPET imaging in rhesus monkeys showed that the relative regional distribution of [C-11]1 and [C-11]4 is consistent with distribution of the NET in the brain, while [F-18]2 and [F-18]3 showed only slight regional differentiation in brain uptake. Especially, the highest ratios of uptake of [C-11]1in NET-rich regions to that in caudate were obtained at 1.30-1.45 at 45 min and remained relatively constant over 85 min. Pretreatment of the monkey with the selective NET inhibitor, desipramine, decreased the specific binding for both ["C]l and [C-11]4. PET imaging in awake monkeys suggested that anesthesia influenced the binding potential of [C-11]1 and [C-11]4 at the NET.

  DOI：

  10.1021/jm800817h