2-(6-Methoxy-pyridin-3-ylmethyl)-1-aza-bicyclo[2.2.2]octan-3-one | 852476-77-8

• 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: 2-(6-Methoxy-pyridin-3-ylmethyl)-1-aza-bicyclo[2.2.2]octan-3-one
• 英文别名: 2-((6-Methoxypyridin-3-yl)methyl)quinuclidin-3-one；2-[(6-methoxypyridin-3-yl)methyl]-1-azabicyclo[2.2.2]octan-3-one
• CAS: 852476-77-8
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: RLXMWRPYOLVUCL-UHFFFAOYSA-N

物化性质

• 沸点：
  388.1±32.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(6-Methoxy-pyridin-3-ylmethyl)-1-aza-bicyclo[2.2.2]octan-3-one 在 aluminum isopropoxide 作用下， 生成
  参考文献：
  名称：

  2-(Arylmethyl)-3-substituted quinuclidines as selective α7 nicotinic receptor ligands

  摘要：

  A series of 2-(arylmethyl)-3-substituted quinuclidines was developed as alpha 7 neuronal nicotinic acetylcholine receptor (nAChR) agonists based on a putative pharmacophore model. The series is highly selective for the alpha 7 over other nAChRs (e.g., the alpha A beta 2 of the CNS, and the muscle and ganglionic subtypes) and is functionally tunable at alpha 7. One member of the series, (+)-N-(1-azabicyclo[2.2.2]oct-3-yl)benzo[b]furan-2-carboxamide (+)-81), has potent agonistic activity for the alpha 7 nAChR (EC50 = 33 nM, I-max = 1.0), at concentrations below those that result in desensitization. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.045
• 作为产物：
  描述：

  3-奎宁环酮 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 生成 2-(6-Methoxy-pyridin-3-ylmethyl)-1-aza-bicyclo[2.2.2]octan-3-one
  参考文献：
  名称：

  2-(Arylmethyl)-3-substituted quinuclidines as selective α7 nicotinic receptor ligands

  摘要：

  A series of 2-(arylmethyl)-3-substituted quinuclidines was developed as alpha 7 neuronal nicotinic acetylcholine receptor (nAChR) agonists based on a putative pharmacophore model. The series is highly selective for the alpha 7 over other nAChRs (e.g., the alpha A beta 2 of the CNS, and the muscle and ganglionic subtypes) and is functionally tunable at alpha 7. One member of the series, (+)-N-(1-azabicyclo[2.2.2]oct-3-yl)benzo[b]furan-2-carboxamide (+)-81), has potent agonistic activity for the alpha 7 nAChR (EC50 = 33 nM, I-max = 1.0), at concentrations below those that result in desensitization. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.045

文献信息

• 2-(Arylmethyl)-3-substituted quinuclidines as selective α7 nicotinic receptor ligands
  作者：Anatoly Mazurov、Jozef Klucik、Lan Miao、Teresa Y. Phillips、Angela Seamans、Jeffrey D. Schmitt、Terry A. Hauser、Raymond T. Johnson、Craig Miller

  DOI：10.1016/j.bmcl.2005.02.045

  日期：2005.4

  A series of 2-(arylmethyl)-3-substituted quinuclidines was developed as alpha 7 neuronal nicotinic acetylcholine receptor (nAChR) agonists based on a putative pharmacophore model. The series is highly selective for the alpha 7 over other nAChRs (e.g., the alpha A beta 2 of the CNS, and the muscle and ganglionic subtypes) and is functionally tunable at alpha 7. One member of the series, (+)-N-(1-azabicyclo[2.2.2]oct-3-yl)benzo[b]furan-2-carboxamide (+)-81), has potent agonistic activity for the alpha 7 nAChR (EC50 = 33 nM, I-max = 1.0), at concentrations below those that result in desensitization. (c) 2005 Elsevier Ltd. All rights reserved.