1-(2-(3-phenylpropoxy)ethyl)pyrrolidine oxalate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-(3-phenylpropoxy)ethyl)pyrrolidine oxalate
• 英文别名: Oxalic acid;1-[2-(3-phenylpropoxy)ethyl]pyrrolidine
• 化学式: C₂H₂O₄*C₁₅H₂₃NO
• 分子量: 323.389
• InChiKey: BQCBLNCPTMSZGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-苯丙醇 、 N-(2-氯乙基)吡咯烷盐酸盐 、 草酸 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙醚 为溶剂， 反应 4.5h， 以22%的产率得到1-(2-(3-phenylpropoxy)ethyl)pyrrolidine oxalate
  参考文献：
  名称：

  Deconstructing 14-phenylpropyloxymetopon: Minimal requirements for binding to mu opioid receptors

  摘要：

  A series of phenylpropyloxyethylamines and cinnamyloxyethylamines were synthesized as deconstructed analogs of 14-phenylpropyloxymetopon and analyzed for opioid receptor binding affinity. Using the Conformationally Sampled Pharmacophore modeling approach, we discovered a series of compounds lacking a tyrosine mimetic, historically considered essential for mu opioid binding. Based on the binding studies, we have identified the optimal analogs to be N-methyl-N-phenylpropyl-2-(3-phenylpropoxy)ethanamine, with 1520 nM, and 2-(cinnamyloxy)-N-methyl-N-phenethylethanamine with 1680 nM affinity for the mu opioid receptor. These partial opioid structure analogs will serve as the novel lead compounds for future optimization studies. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.006

文献信息

• Deconstructing 14-phenylpropyloxymetopon: Minimal requirements for binding to mu opioid receptors
  作者：Lidiya Stavitskaya、Jihyun Shim、Jason R. Healy、Rae R. Matsumoto、Alexander D. MacKerell、Andrew Coop

  DOI：10.1016/j.bmc.2012.05.006

  日期：2012.7

  A series of phenylpropyloxyethylamines and cinnamyloxyethylamines were synthesized as deconstructed analogs of 14-phenylpropyloxymetopon and analyzed for opioid receptor binding affinity. Using the Conformationally Sampled Pharmacophore modeling approach, we discovered a series of compounds lacking a tyrosine mimetic, historically considered essential for mu opioid binding. Based on the binding studies, we have identified the optimal analogs to be N-methyl-N-phenylpropyl-2-(3-phenylpropoxy)ethanamine, with 1520 nM, and 2-(cinnamyloxy)-N-methyl-N-phenethylethanamine with 1680 nM affinity for the mu opioid receptor. These partial opioid structure analogs will serve as the novel lead compounds for future optimization studies. (C) 2012 Elsevier Ltd. All rights reserved.