4-Fluoro-N-(2-piperazin-1-yl-ethyl)-benzamide | 187221-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Fluoro-N-(2-piperazin-1-yl-ethyl)-benzamide
• 英文别名: 4-Fluoro-N-(2-(piperazin-1-yl)ethyl)benzamide；4-fluoro-N-(2-piperazin-1-ylethyl)benzamide
• CAS: 187221-43-8
• 化学式: C₁₃H₁₈FN₃O
• mdl: MFCD11583724
• 分子量: 251.304
• InChiKey: CSEZVRZPXNBVSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  44.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-chlorotetralin 、 4-Fluoro-N-(2-piperazin-1-yl-ethyl)-benzamide 在 potassium carbonate 、 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 24.0h， 以54%的产率得到(+/-)-2-(4-fluorobenzamido)-1-ethyl-4-(1,2,3,4-tetrahydronaphth-1-yl)piperazine
  参考文献：
  名称：

  New Benzocycloalkylpiperazines, Potent and Selective 5-HT_1A Receptor Ligands

  摘要：

  A series of 1-(benzocycloalkyl)-4-(benzamidoalkyl)piperazine derivatives was prepared in order to obtain compounds with a high affinity and selectivity for 5-HT1A receptors. The modifications of aromatic substituents, the length of the alkyl chain, and the size of the ring were explored. Most of N-(1,2,3,4-tetrahydronaphthyl)-N'-(benzamidoethyl)piperazines (32-37) were bound to 5-HT1A receptors in a nanomolar range and presented a high degree of selectivity. After resolution, levorotatory enantiomers showed affinity and selectivity higher than those of dextrorotatory ones for 5-HT1A sites. The agonist type activity of selected derivatives was also confirmed in vitro on the inhibition of the activation of adenylate cyclase induced by forskolin and, in vivo, on the induction of the lower lip retraction in rats.

  DOI：

  10.1021/jm950759z
• 作为产物：
  描述：

  1-氰甲基-4-苯甲基哌嗪 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 水 为溶剂， 反应 10.0h， 生成 4-Fluoro-N-(2-piperazin-1-yl-ethyl)-benzamide
  参考文献：
  名称：

  New Benzocycloalkylpiperazines, Potent and Selective 5-HT_1A Receptor Ligands

  摘要：

  A series of 1-(benzocycloalkyl)-4-(benzamidoalkyl)piperazine derivatives was prepared in order to obtain compounds with a high affinity and selectivity for 5-HT1A receptors. The modifications of aromatic substituents, the length of the alkyl chain, and the size of the ring were explored. Most of N-(1,2,3,4-tetrahydronaphthyl)-N'-(benzamidoethyl)piperazines (32-37) were bound to 5-HT1A receptors in a nanomolar range and presented a high degree of selectivity. After resolution, levorotatory enantiomers showed affinity and selectivity higher than those of dextrorotatory ones for 5-HT1A sites. The agonist type activity of selected derivatives was also confirmed in vitro on the inhibition of the activation of adenylate cyclase induced by forskolin and, in vivo, on the induction of the lower lip retraction in rats.

  DOI：

  10.1021/jm950759z

文献信息

• Dérivés de la napht-1-yl pipérazine, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：ADIR ET COMPAGNIE

  公开号：EP0434561B1

  公开（公告）日：1995-10-18
• New Benzocycloalkylpiperazines, Potent and Selective 5-HT_1A Receptor Ligands
  作者：Youssef El Ahmad、Elisabeth Laurent、Philippe Maillet、Akram Talab、Jean François Teste、Raymond Dokhan、Gilles Tran、Roland Ollivier

  DOI：10.1021/jm950759z

  日期：1997.3.1

  A series of 1-(benzocycloalkyl)-4-(benzamidoalkyl)piperazine derivatives was prepared in order to obtain compounds with a high affinity and selectivity for 5-HT1A receptors. The modifications of aromatic substituents, the length of the alkyl chain, and the size of the ring were explored. Most of N-(1,2,3,4-tetrahydronaphthyl)-N'-(benzamidoethyl)piperazines (32-37) were bound to 5-HT1A receptors in a nanomolar range and presented a high degree of selectivity. After resolution, levorotatory enantiomers showed affinity and selectivity higher than those of dextrorotatory ones for 5-HT1A sites. The agonist type activity of selected derivatives was also confirmed in vitro on the inhibition of the activation of adenylate cyclase induced by forskolin and, in vivo, on the induction of the lower lip retraction in rats.