乙基4-(氨基甲基)-3,6-二氢-1(2H)-吡啶羧酸酯 | 852358-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 乙基4-(氨基甲基)-3,6-二氢-1(2H)-吡啶羧酸酯
• 英文名称: 4-aminomethyl-1-ethoxycarbonyl-1,2,3,6-tetrahydropyridine
• 英文别名: Ethyl 4-(aminomethyl)-5,6-dihydropyridine-1(2H)-carboxylate；ethyl 4-(aminomethyl)-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 852358-79-3
• 化学式: C₉H₁₆N₂O₂
• 分子量: 184.238
• InChiKey: MZCDCLMVCVIIOO-UHFFFAOYSA-N

物化性质

• 沸点：
  273.1±40.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙基4-(氨基甲基)-3,6-二氢-1(2H)-吡啶羧酸酯 在 氢氧化钾 、 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 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 16.5h， 生成 4-amino-5-chloro-2-methoxy-N-[(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
• 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 作用下， 以 乙醇 、 水 、 甲苯 、 苯 为溶剂， 反应 9.5h， 生成 乙基4-(氨基甲基)-3,6-二氢-1(2H)-吡啶羧酸酯
  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

文献信息

• Synthesis and pharmacological evaluation of benzamide derivatives as selective 5-HT4 receptor agonists
  作者：Shuji Sonda、Toshio Kawahara、Kenichi Katayama、Noriko Sato、Kiyoshi Asano

  DOI：10.1016/j.bmc.2005.02.016

  日期：2005.5

  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.