4-[4-[4-(2-ethoxyethoxymethyl)-2-methoxyphenyl]piperazin-1-yl]butyronitrile | 1355460-58-0

• 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: 4-[4-[4-(2-ethoxyethoxymethyl)-2-methoxyphenyl]piperazin-1-yl]butyronitrile
• CAS: 1355460-58-0
• 化学式: C₂₀H₃₁N₃O₃
• 分子量: 361.484
• InChiKey: UNSHQHBHJATOGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  26.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  57.96
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-[4-[4-(2-ethoxyethoxymethyl)-2-methoxyphenyl]piperazin-1-yl]butyronitrile 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 27.0h， 生成 N-[4-[4-[4-(2-ethoxyethoxymethyl)-2-methoxyphenyl]piperazin-1-yl]butyl]benzamide
  参考文献：
  名称：

  Bivalent molecular probes for dopamine D2-like receptors

  摘要：

  Merging two arylamidoalkyl substituted phenylpiperazines as prototypical recognition elements for dopamine D-2-like receptors by oligoethylene glycol linkers led to a series of bivalent ligands. These dimers were investigated in comparison to their monomeric analogues for their dopamine D-2long, D-2short, D-3 and D-4 receptor binding. Radioligand binding experiments revealed strong bivalent effects for some para-substituted benzamide derivatives. For the D-3 subtype, the target compounds 32, 34 and 36 showed an up to 70-fold increase of affinity and a substantial enhancement of subtype selectivity when compared to the monovalent analogue 24. Analysis of the binding curves displayed Hill slopes very close to one indicating that the bivalent ligands displace 1 equiv of radioligand. Obviously, the two pharmacophores occupy an orthosteric and an allosteric binding site rather than adopting a receptor-bridging binding mode. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.063
• 作为产物：
  描述：

  1-bromo-4-(2-ethoxyethoxy)methyl-2-methoxybenzene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 sodium iodide 、 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 42.0h， 生成 4-[4-[4-(2-ethoxyethoxymethyl)-2-methoxyphenyl]piperazin-1-yl]butyronitrile
  参考文献：
  名称：

  Bivalent molecular probes for dopamine D2-like receptors

  摘要：

  Merging two arylamidoalkyl substituted phenylpiperazines as prototypical recognition elements for dopamine D-2-like receptors by oligoethylene glycol linkers led to a series of bivalent ligands. These dimers were investigated in comparison to their monomeric analogues for their dopamine D-2long, D-2short, D-3 and D-4 receptor binding. Radioligand binding experiments revealed strong bivalent effects for some para-substituted benzamide derivatives. For the D-3 subtype, the target compounds 32, 34 and 36 showed an up to 70-fold increase of affinity and a substantial enhancement of subtype selectivity when compared to the monovalent analogue 24. Analysis of the binding curves displayed Hill slopes very close to one indicating that the bivalent ligands displace 1 equiv of radioligand. Obviously, the two pharmacophores occupy an orthosteric and an allosteric binding site rather than adopting a receptor-bridging binding mode. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.063