5-(3-Azabicyclo[3.3.1]non-6-en-7-yl)pyridine-3-carbonitrile | 1403376-75-9

• 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
• 英文名称: 5-(3-Azabicyclo[3.3.1]non-6-en-7-yl)pyridine-3-carbonitrile
• 英文别名: 5-(3-azabicyclo[3.3.1]non-6-en-7-yl)pyridine-3-carbonitrile
• CAS: 1403376-75-9；1403453-46-2；1403453-47-3
• 化学式: C₁₄H₁₅N₃
• 分子量: 225.293
• InChiKey: DEXLAAAKAUMETM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  48.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(3-Azabicyclo[3.3.1]non-6-en-7-yl)pyridine-3-carbonitrile 在 ChiralPak AD-H 50 mm x 250 mm column 作用下， 以 甲醇 、 乙醇 、 二乙胺 为溶剂， 生成 (-)-7-(5-cyanopyridin-3-yl)-3-azabicyclo[3.3.1]non-6-ene hydrochloride salt 、 (-)-7-(5-cyanopyridin-3-yl)-3-azabicyclo[3.3.1]non-6-ene hydrochloride salt
  参考文献：
  名称：

  Structure–Activity Studies of 7-Heteroaryl-3-azabicyclo[3.3.1]non-6-enes: A Novel Class of Highly Potent Nicotinic Receptor Ligands

  摘要：

  The potential for nicotinic ligands with affinity for the alpha 4 beta 2 or alpha 7 subtypes to treat such diverse diseases as nicotine addiction, neuropathic pain, and neurodegenerative and cognitive disorders has been exhibited clinically for several compounds while preclinical activity in relevant in vivo models has been demonstrated for many more. For several therapeutic programs, we sought nicotinic ligands with various combinations of affinity and function across both subtypes, with an emphasis on dual alpha 4 beta 2-alpha 7 ligands, to explore, the possibility of synergistic effects. We report here the structure-activity relationships (SAR) for a novel series of 7-heteroaryl-3-azabicyclo[3.3.1]non-6-enes and characterize many of the analogues for activity at multiple nicotinic subtypes.

  DOI：

  10.1021/jm3011299