(2β,6β)-4-amino-1,2,6-trimethyl-piperidine

• 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: (2β,6β)-4-amino-1,2,6-trimethyl-piperidine
• 英文别名: (2S,6R)-1,2,6-trimethylpiperidin-4-amine
• 化学式: C₈H₁₈N₂
• 分子量: 142.244
• InChiKey: AEQIISCRAPOKNR-DHBOJHSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氨基-5-氯-2-甲氧基苯甲酸 、 (2β,6β)-4-amino-1,2,6-trimethyl-piperidine 在 氯甲酸乙酯 、 三乙胺 作用下， 生成 4-amino-5-chloro-2-methoxy-N-<(2β,4α,6β)-1,2,6-trimethyl-piperidin-4-yl>-benzamide 、 4-amino-5-chloro-2-methoxy-N-<(2β,4β,6β)-1,2,6-trimethyl-piperidin-4-yl>-benzamide
  参考文献：
  名称：

  Structural analysis of 5-HT3 receptor antagonists: synthesis and pharmacological activity of various aromatic esters or amides derived from tropane and 1,2,6-trisubstituted piperidine

  摘要：

  Preliminary results of a structure-activity relationship in the field of 5-HT3 receptor antagonists on the influence of the aromatic ring and steric hindrance around the basic nitrogen atom are reported. The favorable role of the naphthalene moiety substituted by a carbonyl function in position 1 was demonstrated by measuring the biological activity using the inhibition of the specific binding of [H-3]BRL 43694 and the inhibition of the Bezold-Jarisch reflex. Several esters and amides of 1,2,6-trisubstituted piperidine derivatives with a suitable fit with the antagonist reference compounds were synthesized. The lack of biological activity of these compounds emphasizes the importance of steric hindrance for binding with the anionic receptor site. These data confirm the major role of the tropane and quinuclidine frameworks in the potency of a number of 5-HT3 antagonists.

  DOI：

  10.1016/0223-5234(93)90039-h
• 作为产物：
  描述：

  (2S,6R)-1,2,6-trimethylpiperidin-4-one 在 哌啶 、 lithium aluminium tetrahydride 、 硫酸 、 盐酸羟胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 生成 (2β,6β)-4-amino-1,2,6-trimethyl-piperidine
  参考文献：
  名称：

  Structural analysis of 5-HT3 receptor antagonists: synthesis and pharmacological activity of various aromatic esters or amides derived from tropane and 1,2,6-trisubstituted piperidine

  摘要：

  Preliminary results of a structure-activity relationship in the field of 5-HT3 receptor antagonists on the influence of the aromatic ring and steric hindrance around the basic nitrogen atom are reported. The favorable role of the naphthalene moiety substituted by a carbonyl function in position 1 was demonstrated by measuring the biological activity using the inhibition of the specific binding of [H-3]BRL 43694 and the inhibition of the Bezold-Jarisch reflex. Several esters and amides of 1,2,6-trisubstituted piperidine derivatives with a suitable fit with the antagonist reference compounds were synthesized. The lack of biological activity of these compounds emphasizes the importance of steric hindrance for binding with the anionic receptor site. These data confirm the major role of the tropane and quinuclidine frameworks in the potency of a number of 5-HT3 antagonists.

  DOI：

  10.1016/0223-5234(93)90039-h

文献信息

• Structural analysis of 5-HT3 receptor antagonists: synthesis and pharmacological activity of various aromatic esters or amides derived from tropane and 1,2,6-trisubstituted piperidine
  作者：M Langlois、JL Soulier、D Yang、B Bremont、C Florac、V Rampillon、A Giudice

  DOI：10.1016/0223-5234(93)90039-h

  日期：1993.1

  Preliminary results of a structure-activity relationship in the field of 5-HT3 receptor antagonists on the influence of the aromatic ring and steric hindrance around the basic nitrogen atom are reported. The favorable role of the naphthalene moiety substituted by a carbonyl function in position 1 was demonstrated by measuring the biological activity using the inhibition of the specific binding of [H-3]BRL 43694 and the inhibition of the Bezold-Jarisch reflex. Several esters and amides of 1,2,6-trisubstituted piperidine derivatives with a suitable fit with the antagonist reference compounds were synthesized. The lack of biological activity of these compounds emphasizes the importance of steric hindrance for binding with the anionic receptor site. These data confirm the major role of the tropane and quinuclidine frameworks in the potency of a number of 5-HT3 antagonists.