tert-butyl (+/-)-2-endo-3-exo-2-(4-methylphenylsulfonyl)-3-(pyridin-3-yl)oxy-7-azabicyclo[2.2.1]heptane-7-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (+/-)-2-endo-3-exo-2-(4-methylphenylsulfonyl)-3-(pyridin-3-yl)oxy-7-azabicyclo[2.2.1]heptane-7-carboxylate
• 英文别名: tert-butyl (1S,2R,3R,4R)-2-(4-methylphenyl)sulfonyl-3-pyridin-3-yloxy-7-azabicyclo[2.2.1]heptane-7-carboxylate
• 化学式: C₂₃H₂₈N₂O₅S
• 分子量: 444.552
• InChiKey: HQMOWYVKJDKQRW-PLACYPQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  94.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-羟基吡啶 、 tert-butyl (1S,4R)-2-(4-methylphenyl)sulfonyl-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 120.0h， 以38%的产率得到tert-butyl (+/-)-2-endo-3-exo-2-(4-methylphenylsulfonyl)-3-(pyridin-3-yl)oxy-7-azabicyclo[2.2.1]heptane-7-carboxylate
  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