endo-8-methyl-3-(pyridin-3-yl)-8-azabicyclo[3.2.1]octane | 903871-55-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: endo-8-methyl-3-(pyridin-3-yl)-8-azabicyclo[3.2.1]octane
• CAS: 903871-55-6
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: VXELUJNGIVUQQK-CLLJXQQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  16.13
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  endo-8-methyl-3-(pyridin-3-yl)-8-azabicyclo[3.2.1]octane 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以85%的产率得到exo-8-methyl-3-(pyridin-3-yl)-8-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis and binding studies of epibatidine analogues as ligands for the nicotinic acetylcholine receptors

  摘要：

  Neuronal nicotinic acetylcholine receptors (nAChRs) are transmembrane ligand-gated ion channels. Recent research demonstrated that selective nAChR ligands may have therapeutic potential in a number of CNS diseases and disorders. The alkaloid epibatidine is a highly potent non-opioid analgesic and nAChR agonist, but too toxic to be a useful ligand. To develop ligands selective for distinct nAChR subtypes and with reduced toxicity, a series of epibatidine and homoepibatidine analogues were synthesized. (+/-)-8-Methyl-3-(pyridin-3-yl)-8-azabicyclo[3,2,1]oct-2-ene, showed high affinity towards alpha 4 beta 2 (K-i = 2 nM), subtype selectivity (alpha 4 beta 2/alpha 7 affinity ratio > 100) and relatively low toxicity in mice and can be labeled with C-11 and F-18 as positron emission tomography (PET) tracers for imaging of nAChRs. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.01.015
• 作为产物：
  描述：

  exo-8-methyl-3-(pyridin-3-yl)-8-azabicyclo[3.2.1]octan-3-ol 在 palladium on activated charcoal 盐酸 、 二乙胺基三氟化硫 、 氢氟酸 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 37.0h， 生成 endo-8-methyl-3-(pyridin-3-yl)-8-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis and binding studies of epibatidine analogues as ligands for the nicotinic acetylcholine receptors

  摘要：

  Neuronal nicotinic acetylcholine receptors (nAChRs) are transmembrane ligand-gated ion channels. Recent research demonstrated that selective nAChR ligands may have therapeutic potential in a number of CNS diseases and disorders. The alkaloid epibatidine is a highly potent non-opioid analgesic and nAChR agonist, but too toxic to be a useful ligand. To develop ligands selective for distinct nAChR subtypes and with reduced toxicity, a series of epibatidine and homoepibatidine analogues were synthesized. (+/-)-8-Methyl-3-(pyridin-3-yl)-8-azabicyclo[3,2,1]oct-2-ene, showed high affinity towards alpha 4 beta 2 (K-i = 2 nM), subtype selectivity (alpha 4 beta 2/alpha 7 affinity ratio > 100) and relatively low toxicity in mice and can be labeled with C-11 and F-18 as positron emission tomography (PET) tracers for imaging of nAChRs. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.01.015