3-(aminomethyl)-N-methyl-1-azabicyclo[2.2.2]octan-3-amine | 313643-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: 3-(aminomethyl)-N-methyl-1-azabicyclo[2.2.2]octan-3-amine
• CAS: 313643-47-9
• 化学式: C₉H₁₉N₃
• 分子量: 169.27
• InChiKey: ZVRJOAKGHJJQHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N'-羰基二咪唑 、 3-(aminomethyl)-N-methyl-1-azabicyclo[2.2.2]octan-3-amine 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 1'-Methylspiro[1-azabicyclo[2.2.2]octane-3,5'-imidazolidine]-2'-one
  参考文献：
  名称：

  (−)-Spiro[1-azabicyclo[2.2.2]octane-3,5‘-oxazolidin-2‘-one], a Conformationally Restricted Analogue of Acetylcholine, Is a Highly Selective Full Agonist at the α7 Nicotinic Acetylcholine Receptor

  摘要：

  Neuronal nicotinic acetylcholine receptors are members of the ligand-gated ion channel receptor superfamily and may play important roles in modulating neurotransmission, cognition, sensory gating, and anxiety. Because of its distribution and abundance in the CNS, the alpha7 nicotinic receptor is a strong candidate to be involved in some of these functions. In this paper we describe the synthesis and in vitro profile of AR-R17779, (-)-spiro[1-azabicyclo[2.2.2]octane-3,5'-oxazolidin-2'-one] (4a), a potent full agonist at the rat alpha7 nicotinic receptor, which is highly selective for the rat alpha7 nicotinic receptor over the alpha4 beta2 subtype. Preliminary SAR of AR-R17779 presented here indicate that there is little scope for modification of this rigid molecule as even minor changes result in significant loss of the alpha7 nicotinic receptor affinity.

  DOI：

  10.1021/jm000249r
• 作为产物：
  描述：

  1-Azabicyclo[2.2.2]octane-3-carbonitrile, 3-(methylamino) 在 镍 氨 、 氢气 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以91%的产率得到3-(aminomethyl)-N-methyl-1-azabicyclo[2.2.2]octan-3-amine
  参考文献：
  名称：

  (−)-Spiro[1-azabicyclo[2.2.2]octane-3,5‘-oxazolidin-2‘-one], a Conformationally Restricted Analogue of Acetylcholine, Is a Highly Selective Full Agonist at the α7 Nicotinic Acetylcholine Receptor

  摘要：

  Neuronal nicotinic acetylcholine receptors are members of the ligand-gated ion channel receptor superfamily and may play important roles in modulating neurotransmission, cognition, sensory gating, and anxiety. Because of its distribution and abundance in the CNS, the alpha7 nicotinic receptor is a strong candidate to be involved in some of these functions. In this paper we describe the synthesis and in vitro profile of AR-R17779, (-)-spiro[1-azabicyclo[2.2.2]octane-3,5'-oxazolidin-2'-one] (4a), a potent full agonist at the rat alpha7 nicotinic receptor, which is highly selective for the rat alpha7 nicotinic receptor over the alpha4 beta2 subtype. Preliminary SAR of AR-R17779 presented here indicate that there is little scope for modification of this rigid molecule as even minor changes result in significant loss of the alpha7 nicotinic receptor affinity.

  DOI：

  10.1021/jm000249r

文献信息

• (−)-Spiro[1-azabicyclo[2.2.2]octane-3,5‘-oxazolidin-2‘-one], a Conformationally Restricted Analogue of Acetylcholine, Is a Highly Selective Full Agonist at the α7 Nicotinic Acetylcholine Receptor
  作者：George Mullen、James Napier、Michael Balestra、Thomas DeCory、Gregory Hale、John Macor、Robert Mack、James Loch、Ed Wu、Alexander Kover、Patrick Verhoest、Anthony Sampognaro、Eifion Phillips、Yanyi Zhu、Robert Murray、Ronald Griffith、James Blosser、David Gurley、Anthony Machulskis、John Zongrone、Alan Rosen、Jack Gordon

  DOI：10.1021/jm000249r

  日期：2000.11.1

  Neuronal nicotinic acetylcholine receptors are members of the ligand-gated ion channel receptor superfamily and may play important roles in modulating neurotransmission, cognition, sensory gating, and anxiety. Because of its distribution and abundance in the CNS, the alpha7 nicotinic receptor is a strong candidate to be involved in some of these functions. In this paper we describe the synthesis and in vitro profile of AR-R17779, (-)-spiro[1-azabicyclo[2.2.2]octane-3,5'-oxazolidin-2'-one] (4a), a potent full agonist at the rat alpha7 nicotinic receptor, which is highly selective for the rat alpha7 nicotinic receptor over the alpha4 beta2 subtype. Preliminary SAR of AR-R17779 presented here indicate that there is little scope for modification of this rigid molecule as even minor changes result in significant loss of the alpha7 nicotinic receptor affinity.