4-amino-5-chloro-2-methoxy-N-[1-ethoxycarbonyl-(1,2,3,6-tetrahydropyridin)-4-ylmethyl]benzamide | 852358-80-6

• 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-amino-5-chloro-2-methoxy-N-[1-ethoxycarbonyl-(1,2,3,6-tetrahydropyridin)-4-ylmethyl]benzamide
• CAS: 852358-80-6
• 化学式: C₁₇H₂₂ClN₃O₄
• 分子量: 367.832
• InChiKey: HFHJSGNOEXCSFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  93.89
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-amino-5-chloro-2-methoxy-N-[1-ethoxycarbonyl-(1,2,3,6-tetrahydropyridin)-4-ylmethyl]benzamide 在 氢氧化钾 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 2.5h， 生成 4-Amino-5-chloro-2-methoxy-N-[1-(6-oxo-6-phenyl-hexyl)-1,2,3,6-tetrahydro-pyridin-4-ylmethyl]-benzamide
  参考文献：
  名称：

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

  摘要：

  It is thought that selective 5-HT4 receptor agonists-such as 4-amino-5-chloro-2-metboxy-N-[1-(6-oxo-6-phenylhexyl)piperidin-4-ylmethyl]benzamide (2)-have the ability to enhance both upper and lower gastrointestinal motility without any significant adverse effects.Modification of 2 was performed. Variation of the piperidin-4-ylmethyl moiety of 2 led to a decrease in the binding affinity for the 5-HT4 receptor. Following conversion of the carbonyl group on the benzoyl part to a hydroxyl or sulfoxide group, the binding affinity for the 5-HT4 receptor was retained although the effect on defecation was reduced. Many of the 4-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamides that had a ether or sulfide moiety in the side-chain part at the 1-position of the piperidine exhibited high affinity for the 5-HT4 receptor.Among these, phenylthio 41c and benzylthio derivative 44 were selective 5-HT4 receptor agonists, and had a similar effect on defecation to compound 2. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.016
• 作为产物：
  描述：

  N-乙氧羰基-4-哌啶酮 在 sodium ethanolate 、 phosphorus pentoxide 、 铁粉 、 氯化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 23.5h， 生成 4-amino-5-chloro-2-methoxy-N-[1-ethoxycarbonyl-(1,2,3,6-tetrahydropyridin)-4-ylmethyl]benzamide
  参考文献：
  名称：

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

  摘要：

  It is thought that selective 5-HT4 receptor agonists-such as 4-amino-5-chloro-2-metboxy-N-[1-(6-oxo-6-phenylhexyl)piperidin-4-ylmethyl]benzamide (2)-have the ability to enhance both upper and lower gastrointestinal motility without any significant adverse effects.Modification of 2 was performed. Variation of the piperidin-4-ylmethyl moiety of 2 led to a decrease in the binding affinity for the 5-HT4 receptor. Following conversion of the carbonyl group on the benzoyl part to a hydroxyl or sulfoxide group, the binding affinity for the 5-HT4 receptor was retained although the effect on defecation was reduced. Many of the 4-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamides that had a ether or sulfide moiety in the side-chain part at the 1-position of the piperidine exhibited high affinity for the 5-HT4 receptor.Among these, phenylthio 41c and benzylthio derivative 44 were selective 5-HT4 receptor agonists, and had a similar effect on defecation to compound 2. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.016