(R)-N-methyl-3-(2-hydroxyphenoxy)-3-phenyl-1-propylamine | 862183-41-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-N-methyl-3-(2-hydroxyphenoxy)-3-phenyl-1-propylamine
• 英文别名: (R)-O-nornisoxetine；2-[(1R)-3-(methylamino)-1-phenylpropoxy]phenol
• CAS: 862183-41-3
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: DJMWQVUXPYUHBF-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-N-methyl-3-(2-hydroxyphenoxy)-3-phenyl-1-propylamine 、 [11C]methyl iodide 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 (R)-[O-methyl-11C]nisoxetine 、
  参考文献：
  名称：

  Synthesis and C-11 labeling of three potent norepinephrine transporter selective ligands ((R)-nisoxetine, lortalamine, and oxaprotiline) for comparative PET studies in baboons

  摘要：

  Three potent antidepressants, (R)-nisoxetine, lortalamine, and oxaprotiline, with high affinity and high selectivity for the norepinephrine transporter (NET) were synthesized and radiolabeled with C-11 via [C-11]methylation. The reference compounds and their corresponding normethyl precursors were synthesized via multi-step synthetic approaches. The radiochemical syntheses were performed by simple alkylation of the corresponding normethyl precursors with no-carrier-added [C-11]CH3I in DMF. After HPLC purification, (R)-[N-(CH3)-C-1]nisoxetine, [C-11]lortalamine, and [1 v C]oxaprotiline were obtained in 63-97% radiochemical yields, whereas (R)-[O-(CH3)-C-11]nisoxetine was obtained in 23-29% radiochemical yields due to substantial formation of the undesired N-[C-11]methylated byproduct (64-70%). These C-11 labeled tracers allowed us to carry out comparative studies of NET in baboons with positron emission tomography (PET) and evaluate their potential as PET tracers for imaging brain NET. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2005.04.062
• 作为产物：
  描述：

  (R)-1-iodo-3-(2-mesyloxyphenoxy)-3-phenylpropane 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 (R)-N-methyl-3-(2-hydroxyphenoxy)-3-phenyl-1-propylamine
  参考文献：
  名称：

  Synthesis and C-11 labeling of three potent norepinephrine transporter selective ligands ((R)-nisoxetine, lortalamine, and oxaprotiline) for comparative PET studies in baboons

  摘要：

  Three potent antidepressants, (R)-nisoxetine, lortalamine, and oxaprotiline, with high affinity and high selectivity for the norepinephrine transporter (NET) were synthesized and radiolabeled with C-11 via [C-11]methylation. The reference compounds and their corresponding normethyl precursors were synthesized via multi-step synthetic approaches. The radiochemical syntheses were performed by simple alkylation of the corresponding normethyl precursors with no-carrier-added [C-11]CH3I in DMF. After HPLC purification, (R)-[N-(CH3)-C-1]nisoxetine, [C-11]lortalamine, and [1 v C]oxaprotiline were obtained in 63-97% radiochemical yields, whereas (R)-[O-(CH3)-C-11]nisoxetine was obtained in 23-29% radiochemical yields due to substantial formation of the undesired N-[C-11]methylated byproduct (64-70%). These C-11 labeled tracers allowed us to carry out comparative studies of NET in baboons with positron emission tomography (PET) and evaluate their potential as PET tracers for imaging brain NET. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2005.04.062

文献信息

• Synthesis and C-11 labeling of three potent norepinephrine transporter selective ligands ((R)-nisoxetine, lortalamine, and oxaprotiline) for comparative PET studies in baboons
  作者：Kuo-Shyan Lin、Yu-Shin Ding

  DOI：10.1016/j.bmc.2005.04.062

  日期：2005.8

  Three potent antidepressants, (R)-nisoxetine, lortalamine, and oxaprotiline, with high affinity and high selectivity for the norepinephrine transporter (NET) were synthesized and radiolabeled with C-11 via [C-11]methylation. The reference compounds and their corresponding normethyl precursors were synthesized via multi-step synthetic approaches. The radiochemical syntheses were performed by simple alkylation of the corresponding normethyl precursors with no-carrier-added [C-11]CH3I in DMF. After HPLC purification, (R)-[N-(CH3)-C-1]nisoxetine, [C-11]lortalamine, and [1 v C]oxaprotiline were obtained in 63-97% radiochemical yields, whereas (R)-[O-(CH3)-C-11]nisoxetine was obtained in 23-29% radiochemical yields due to substantial formation of the undesired N-[C-11]methylated byproduct (64-70%). These C-11 labeled tracers allowed us to carry out comparative studies of NET in baboons with positron emission tomography (PET) and evaluate their potential as PET tracers for imaging brain NET. Published by Elsevier Ltd.