3-[2-(S)-N-tert-butoxycarbonyl-2-pyrrolinemethoxy]-5-bromopyridine | 1415394-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-[2-(S)-N-tert-butoxycarbonyl-2-pyrrolinemethoxy]-5-bromopyridine
• 英文别名: tert-butyl (2S)-2-[(5-bromopyridin-3-yl)oxymethyl]-2,5-dihydropyrrole-1-carboxylate
• CAS: 1415394-66-9
• 化学式: C₁₅H₁₉BrN₂O₃
• 分子量: 355.231
• InChiKey: KDMTZUYRHJUIMY-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[2-(S)-N-tert-butoxycarbonyl-2-pyrrolinemethoxy]-5-bromopyridine 、 六正丁基二锡 在 四(三苯基膦)钯 、 三乙胺 作用下， 以5 mg的产率得到5-tributyltin-3-[2-{(S)-N-tert-butoxycarbonyl-3-pyrrolinyl}methoxy]pyridine
  参考文献：
  名称：

  Synthesis and evaluation of 3-123I-iodo-5-[2-(S)-3-pyrrolinylmethoxy]-pyridine (niodene) as a potential nicotinic α4β2 receptor imaging agent

  摘要：

  Nicotinic acetylcholine receptors (nAChRs) are downregulated in disease conditions such as Alzheimer's and substance abuse. Presently, I-123-5-IA-85380 is used in human studies and requires over 6 h of scanning time, thus increases patient discomfort. We have designed and synthesized 3-iodo-5-[2-(S)-3-pyrrolinylmethoxy]pyridine (niodene) with the aim to have faster binding kinetics compared to I-123-5-IA-85380, which may reduce scanning time and help in imaging studies. Binding affinity K-i of niodene for rat brain alpha 4 beta 2 receptors in brain homogenate assays using H-3-cytisine was 0.27 nM. Niodene, 10 nM displaced >95% of F-18-nifene bound to alpha 4 beta 2 receptors in rat brain slices. By using the iododestannylation method, I-123-niodene was obtained in high radiochemical purity (>95%) but with low radiochemical yield (<5%) and low specific activity (similar to 100 Ci/mmol). Autoradiograms show I-123-niodene localized in the thalamus and cortex, which was displaced by nicotine (thalamus to cerebellum ratio = 4; cortex to cerebellum ratio = 1.6). Methods of radioiodination need to be further evaluated in order to obtain I-123-niodene in higher radiochemical yields and higher specific activity of this potentially useful new SPECT imaging agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.012
• 作为产物：
  描述：

  3-溴-5-羟基吡啶 、 (S)-tert-butyl 2-(hydroxymethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到3-[2-(S)-N-tert-butoxycarbonyl-2-pyrrolinemethoxy]-5-bromopyridine
  参考文献：
  名称：

  Synthesis and evaluation of 3-123I-iodo-5-[2-(S)-3-pyrrolinylmethoxy]-pyridine (niodene) as a potential nicotinic α4β2 receptor imaging agent

  摘要：

  Nicotinic acetylcholine receptors (nAChRs) are downregulated in disease conditions such as Alzheimer's and substance abuse. Presently, I-123-5-IA-85380 is used in human studies and requires over 6 h of scanning time, thus increases patient discomfort. We have designed and synthesized 3-iodo-5-[2-(S)-3-pyrrolinylmethoxy]pyridine (niodene) with the aim to have faster binding kinetics compared to I-123-5-IA-85380, which may reduce scanning time and help in imaging studies. Binding affinity K-i of niodene for rat brain alpha 4 beta 2 receptors in brain homogenate assays using H-3-cytisine was 0.27 nM. Niodene, 10 nM displaced >95% of F-18-nifene bound to alpha 4 beta 2 receptors in rat brain slices. By using the iododestannylation method, I-123-niodene was obtained in high radiochemical purity (>95%) but with low radiochemical yield (<5%) and low specific activity (similar to 100 Ci/mmol). Autoradiograms show I-123-niodene localized in the thalamus and cortex, which was displaced by nicotine (thalamus to cerebellum ratio = 4; cortex to cerebellum ratio = 1.6). Methods of radioiodination need to be further evaluated in order to obtain I-123-niodene in higher radiochemical yields and higher specific activity of this potentially useful new SPECT imaging agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.012

文献信息

• Synthesis and evaluation of 3-123I-iodo-5-[2-(S)-3-pyrrolinylmethoxy]-pyridine (niodene) as a potential nicotinic α4β2 receptor imaging agent
  作者：Suresh K. Pandey、Shawn Pan、Ritu Kant、Sharon A. Kuruvilla、Min-Liang Pan、Jogeshwar Mukherjee

  DOI：10.1016/j.bmcl.2012.10.012

  日期：2012.12

  Nicotinic acetylcholine receptors (nAChRs) are downregulated in disease conditions such as Alzheimer's and substance abuse. Presently, I-123-5-IA-85380 is used in human studies and requires over 6 h of scanning time, thus increases patient discomfort. We have designed and synthesized 3-iodo-5-[2-(S)-3-pyrrolinylmethoxy]pyridine (niodene) with the aim to have faster binding kinetics compared to I-123-5-IA-85380, which may reduce scanning time and help in imaging studies. Binding affinity K-i of niodene for rat brain alpha 4 beta 2 receptors in brain homogenate assays using H-3-cytisine was 0.27 nM. Niodene, 10 nM displaced >95% of F-18-nifene bound to alpha 4 beta 2 receptors in rat brain slices. By using the iododestannylation method, I-123-niodene was obtained in high radiochemical purity (>95%) but with low radiochemical yield (<5%) and low specific activity (similar to 100 Ci/mmol). Autoradiograms show I-123-niodene localized in the thalamus and cortex, which was displaced by nicotine (thalamus to cerebellum ratio = 4; cortex to cerebellum ratio = 1.6). Methods of radioiodination need to be further evaluated in order to obtain I-123-niodene in higher radiochemical yields and higher specific activity of this potentially useful new SPECT imaging agent. (C) 2012 Elsevier Ltd. All rights reserved.