N-(6-(4-(2-methoxyphenyl)piperazin-1-yl)hexyl)-2-naphthamide | 1247869-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(6-(4-(2-methoxyphenyl)piperazin-1-yl)hexyl)-2-naphthamide
• 英文别名: N-[6-[4-(2-methoxyphenyl)piperazin-1-yl]hexyl]naphthalene-2-carboxamide
• CAS: 1247869-22-2
• 化学式: C₂₈H₃₅N₃O₂
• 分子量: 445.605
• InChiKey: GNQMAWAOPDTCCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 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-(6-aminohexyl)-1-(2-methoxyphenyl)piperazine 、 2-萘甲酰氯 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 N-(6-(4-(2-methoxyphenyl)piperazin-1-yl)hexyl)-2-naphthamide
  参考文献：
  名称：

  Synthesis and in vitro binding studies of piperazine-alkyl-naphthamides: Impact of homology and sulphonamide/carboxamide bioisosteric replacement on the affinity for 5-HT1A, α2A, D4.2, D3 and D2L receptors

  摘要：

  A series of carboxamide and sulphonamide alkyl(ethyl to hexyl) piperazine analogues were prepared and tested for their affinity to bind to a range of receptors potentially involved in psychiatric disorders. These chemical modifications led us to explore the impact of homology and bioisosteric replacement of the amide group. All of these compounds possessed a high affinity for 5-HT1A receptors, irrespective of the size of the linker, the carboxamide derivative with a pentyl linker had the highest affinity for alpha(2A) receptor sites and also a high affinity for 5-HT1A and D3 receptors. The sulphonamide analogue with a hexyl linker possessed a high affinity for 5-HT1A, D4.2 and D3 receptors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.002

文献信息

• Synthesis and in vitro binding studies of piperazine-alkyl-naphthamides: Impact of homology and sulphonamide/carboxamide bioisosteric replacement on the affinity for 5-HT1A, α2A, D4.2, D3 and D2L receptors
  作者：Mélissa Résimont、Jean-François Liégeois

  DOI：10.1016/j.bmcl.2010.07.002

  日期：2010.9

  A series of carboxamide and sulphonamide alkyl(ethyl to hexyl) piperazine analogues were prepared and tested for their affinity to bind to a range of receptors potentially involved in psychiatric disorders. These chemical modifications led us to explore the impact of homology and bioisosteric replacement of the amide group. All of these compounds possessed a high affinity for 5-HT1A receptors, irrespective of the size of the linker, the carboxamide derivative with a pentyl linker had the highest affinity for alpha(2A) receptor sites and also a high affinity for 5-HT1A and D3 receptors. The sulphonamide analogue with a hexyl linker possessed a high affinity for 5-HT1A, D4.2 and D3 receptors. (C) 2010 Elsevier Ltd. All rights reserved.