N-{4-[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-pyridin-4-yl-acetamide | 1382482-03-2

• 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: N-{4-[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-pyridin-4-yl-acetamide
• 英文别名: N-[4-[2-(4-phenylpiperazin-1-yl)ethyl]phenyl]-2-pyridin-4-ylacetamide
• CAS: 1382482-03-2
• 化学式: C₂₅H₂₈N₄O
• 分子量: 400.524
• InChiKey: YNPWPCIYPGTMBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(4-nitrophenyl)-1-(4-phenylpiperazin-1-yl)ethanone 在 一水合肼 、 1-丙基磷酸酐 、 三乙胺 、 diborane(6) 作用下， 以 四氢呋喃 、 乙醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 N-{4-[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-pyridin-4-yl-acetamide
  参考文献：
  名称：

  Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D2 and 5-hydroxytryptamine 5HT1A receptors

  摘要：

  It is suggested that the ratio of dopamine D-2 to 5-hydroxytryptamine 5-HT1A activity is an important parameter that determines the efficiency of antipsychotic drugs. Here we present the synthesis of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas and their structure-activity relationship studies on dopamine D-2 and 5-hydrohytryptamine 5-HT1A receptors. It was shown that ligand selectivity and affinity strongly depends on their topology and the presence of a pyridyl group in the head of molecules. Molecular modeling studies using homology modeling and docking simulation revealed a rational explanation for the ligand behavior. The observed binding modes and receptor-ligand interactions provided us with a clue for optimizing the optimal selectivity towards 5-HT1A receptors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.098

文献信息

• Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D2 and 5-hydroxytryptamine 5HT1A receptors
  作者：Vladimir Sukalovic、Djurdjica Ignjatovic、Gordana Tovilovic、Deana Andric、Kaveh Shakib、Sladjana Kostic-Rajacic、Vukic Soskic

  DOI：10.1016/j.bmcl.2012.04.098

  日期：2012.6

  It is suggested that the ratio of dopamine D-2 to 5-hydroxytryptamine 5-HT1A activity is an important parameter that determines the efficiency of antipsychotic drugs. Here we present the synthesis of N-[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas and their structure-activity relationship studies on dopamine D-2 and 5-hydrohytryptamine 5-HT1A receptors. It was shown that ligand selectivity and affinity strongly depends on their topology and the presence of a pyridyl group in the head of molecules. Molecular modeling studies using homology modeling and docking simulation revealed a rational explanation for the ligand behavior. The observed binding modes and receptor-ligand interactions provided us with a clue for optimizing the optimal selectivity towards 5-HT1A receptors. (C) 2012 Elsevier Ltd. All rights reserved.