4-amino-N-[(1-benzyl-4-piperidinyl)methyl]-5-chlorobenzamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-amino-N-[(1-benzyl-4-piperidinyl)methyl]-5-chlorobenzamide
• 英文别名: 4-amino-N-[(1-benzylpiperidin-4-yl)methyl]-3-chlorobenzamide
• 化学式: C₂₀H₂₄ClN₃O
• 分子量: 357.883
• InChiKey: QOGBYENUVJLFGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  58.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-苄基哌啶-4-羧酰胺 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4-amino-N-[(1-benzyl-4-piperidinyl)methyl]-5-chlorobenzamide
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of carboxamide derivatives as selective serotoninergic 5-HT4 receptor agonists

  摘要：

  A number of new carboxamide derivatives were synthesized. The affinity of these compounds for the serotoninergic 5-HT4 receptor was evaluated by use of radioligand-binding techniques. The agonistic activity was evaluated as the contractile effect of the ascending colon isolated from guinea-pigs. Among these compounds, 4-amino-5-chloro-2-methoxy-N-[1-[2-[(methylsulfonyl)amino]ethyl]-4-piperidinylmethyl]benzamide (24) showed a high affinity for the 5-HT4 receptor (Ki = 9.6 nM). Compound 24 displayed a higher affinity for 5-HT4 receptors than the other receptors, including, 5-HT3 and dopamine D-2 receptors. In addition, compound 24 was confirmed to be a potent 5-HT4 receptor agonist (ED50 = 7.0 nM). An interaction model between compound 24 and 5-HT4 receptor was proposed. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00158-0

文献信息

• Synthesis and pharmacological evaluation of carboxamide derivatives as selective serotoninergic 5-HT4 receptor agonists
  作者：Katsuhiko Itoh、Koji Kanzaki、Tsuguo Ikebe、Takanobu Kuroita、Hideo Tomozane、Shuji Sonda、Noriko Sato、Keiichiro Haga、Takeshi Kawakita

  DOI：10.1016/s0223-5234(99)80083-x

  日期：1999.4

  A number of new carboxamide derivatives were synthesized. The affinity of these compounds for the serotoninergic 5-HT4 receptor was evaluated by use of radioligand-binding techniques. The agonistic activity was evaluated as the contractile effect of the ascending colon isolated from guinea-pigs. Among these compounds, 4-amino-5-chloro-2-methoxy-N-[1-[2-[(methylsulfonyl)amino]ethly]-4-piperidinylmethyl]benzamide (24) showed a high affinity for the 5-HT4 receptor (Ki = 9.6 nM). Compound 24 displayed a higher affinity for 5-HT4 receptors than the other receptors, including, 5-HT3 and dopamine D-2 receptors. In addition, compound 24 was confirmed to be a potent 5-HT4 receptor agonist (ED50 - 7.0 nM). An interaction model between compound 24 and 5-HT4 receptor was proposed. (C) Elsevier, Paris.