N-{4-[4-(2-methoxyphenyl)piperazin-1-yl]phenyl}acetamide | 1128086-08-7

• 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-[4-(2-methoxyphenyl)piperazin-1-yl]phenyl}acetamide
• 英文别名: N-[4-[4-(2-methoxyphenyl)piperazin-1-yl]phenyl]acetamide
• CAS: 1128086-08-7
• 化学式: C₁₉H₂₃N₃O₂
• 分子量: 325.411
• InChiKey: BLSOWZPRYVSKEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-[4-(2-methoxyphenyl)piperazin-1-yl]phenylamine 、 乙酸酐 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到N-{4-[4-(2-methoxyphenyl)piperazin-1-yl]phenyl}acetamide
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of new arylpiperazines N-{4-[4-(aryl) piperazine-1-yl]-phenyl}-amine derivatives: Putative role of 5-HT1A receptors

  摘要：

  In an attempt to design novel 5-HT1A agonists/partial agonists, based on an arylpiperazine nucleus, a series of N-{4-[4-(aryl) piperazine-1-yl]-phenyl}-amine derivatives were synthesized and biologically tested. The anxiolytic effect of the compounds was investigated employing the Elevated plus Maze (EPM) task. On the basis of in vivo functional test, compound 1c (3 mg/kg) and 4c (3 mg/kg) induced significant increments in open arm entries and time on EPM as compared to Buspirone. The anxiolytic effects of compounds 1c and 4c were effectively antagonized by WAY-100635, a 5-HT1A receptor antagonist (0.5 mg/kg). Furthermore, we have also evaluated the concentration of 5-HT in the brain tissue using HPLC with fluorescent detection. Our result showed that serotonin levels were significantly decreased by similar to 38% (p < 0.001) and similar to 32% (p < 0.001) after acute administration of compounds 1c and 4c, respectively. These findings suggest that the anxiolytic like activity of these new arylpiperazines is mediated via 5-HT1A receptors in the brain. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.043

文献信息

• Synthesis and pharmacological evaluation of new arylpiperazines N-{4-[4-(aryl) piperazine-1-yl]-phenyl}-amine derivatives: Putative role of 5-HT1A receptors
  作者：Manisha Khatri、Santosh Kumar Rai、Sameena Alam、Anjana Vij、Manisha Tiwari

  DOI：10.1016/j.bmc.2009.01.043

  日期：2009.3

  In an attempt to design novel 5-HT1A agonists/partial agonists, based on an arylpiperazine nucleus, a series of N-4-[4-(aryl) piperazine-1-yl]-phenyl}-amine derivatives were synthesized and biologically tested. The anxiolytic effect of the compounds was investigated employing the Elevated plus Maze (EPM) task. On the basis of in vivo functional test, compound 1c (3 mg/kg) and 4c (3 mg/kg) induced significant increments in open arm entries and time on EPM as compared to Buspirone. The anxiolytic effects of compounds 1c and 4c were effectively antagonized by WAY-100635, a 5-HT1A receptor antagonist (0.5 mg/kg). Furthermore, we have also evaluated the concentration of 5-HT in the brain tissue using HPLC with fluorescent detection. Our result showed that serotonin levels were significantly decreased by similar to 38% (p < 0.001) and similar to 32% (p < 0.001) after acute administration of compounds 1c and 4c, respectively. These findings suggest that the anxiolytic like activity of these new arylpiperazines is mediated via 5-HT1A receptors in the brain. (C) 2009 Elsevier Ltd. All rights reserved.