1-[4-(3-methoxyphenyl)butyl]-4-phenylpiperazine | 1610999-41-1

• 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: 1-[4-(3-methoxyphenyl)butyl]-4-phenylpiperazine
• CAS: 1610999-41-1
• 化学式: C₂₁H₂₈N₂O
• 分子量: 324.466
• InChiKey: RIESGYNOLFLRSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  15.71
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-[4-(3-methoxyphenyl)butyl]-4-phenylpiperazine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以73%的产率得到3-[4-(4-phenylpiperazin-1-yl)butyl]phenol
  参考文献：
  名称：

  Towards the development of 5-HT7 ligands combining serotonin-like and arylpiperazine moieties

  摘要：

  Many known 5-HT7 ligands contain either a serotonin-like or an arylpiperazine structure that, in published SAR studies, are generally supposed to bind the same receptor pocket. Conversely, we explored the hypothesis that two such moieties can co-exist in the same ligand, binding to different pockets. We thus designed and synthesized a set of compounds including both a 5-hydroxyindol-3-ylethyl and a 1-arylpiperazine moieties connected by a short linker. The compounds were tested for their affinity for human 5-HT7 serotonin receptor. We further prepared a novel series of 5-HT7 ligands, where the 5-hydroxyindol-3-ylethyl moiety was bioisosterically replaced by a 3-hydroxyanilinoalkyl one. Among the newly synthesized compounds, potent ligands at the 5-HT7 receptor, behaving as antagonists in functional tests, were identified, even if they showed limited subtype selectivity. Docking studies within a model of the 5-HT7 receptor showed that the binding site can actually accommodate both moieties, with the serotonin-like one in the putative orthosteric site and the arylpiperazine one occupying an accessory pocket. The present results demonstrate that it is possible to devise and develop new 5-HT7 ligands merging two privileged structures in the same molecule.

  DOI：

  10.1016/j.ejmech.2014.04.034
• 作为产物：
  描述：

  4-(3-methoxyphenyl)-1-(4-phenylpiperazin-1-yl)butan-1-one 在 diborane(6) 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以67%的产率得到1-[4-(3-methoxyphenyl)butyl]-4-phenylpiperazine
  参考文献：
  名称：

  Towards the development of 5-HT7 ligands combining serotonin-like and arylpiperazine moieties

  摘要：

  Many known 5-HT7 ligands contain either a serotonin-like or an arylpiperazine structure that, in published SAR studies, are generally supposed to bind the same receptor pocket. Conversely, we explored the hypothesis that two such moieties can co-exist in the same ligand, binding to different pockets. We thus designed and synthesized a set of compounds including both a 5-hydroxyindol-3-ylethyl and a 1-arylpiperazine moieties connected by a short linker. The compounds were tested for their affinity for human 5-HT7 serotonin receptor. We further prepared a novel series of 5-HT7 ligands, where the 5-hydroxyindol-3-ylethyl moiety was bioisosterically replaced by a 3-hydroxyanilinoalkyl one. Among the newly synthesized compounds, potent ligands at the 5-HT7 receptor, behaving as antagonists in functional tests, were identified, even if they showed limited subtype selectivity. Docking studies within a model of the 5-HT7 receptor showed that the binding site can actually accommodate both moieties, with the serotonin-like one in the putative orthosteric site and the arylpiperazine one occupying an accessory pocket. The present results demonstrate that it is possible to devise and develop new 5-HT7 ligands merging two privileged structures in the same molecule.

  DOI：

  10.1016/j.ejmech.2014.04.034