3α-benzoyloxy-8-phenetyl-8-azabicyclo[3.2.1]octane | 1361089-14-6

• 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: 3α-benzoyloxy-8-phenetyl-8-azabicyclo[3.2.1]octane
• CAS: 1361089-14-6
• 化学式: C₂₂H₂₅NO₂
• 分子量: 335.446
• InChiKey: ZVQCTZVWEBSXKK-WKCHPHFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3α-benzoyloxy-8-phenetyl-8-azabicyclo[3.2.1]octane 在 盐酸 作用下， 以 乙醚 为溶剂， 以232 mg的产率得到3α-benzoyloxy-8-phenetyl-8-azabicyclo[3.2.1]octane hydrochloride
  参考文献：
  名称：

  Structure-based design, synthesis and structure–activity relationships of dibenzosuberyl- and benzoate-substituted tropines as ligands for acetylcholine-binding protein

  摘要：

  Using structure-based optimization procedures on in silico hits, dibenzosuberyl- and benzoate substituted tropines were designed as ligands for acetylcholine-binding protein (AChBP). This protein is a homolog to the ligand binding domain of the nicotinic acetylcholine receptor (nAChR). Distinct SAR is observed between two AChBP species variants and between the alpha 7 and alpha 4 beta 2 nAChR subtype. The AChBP species differences are indicative of a difference in accessibility of a ligand-inducible subpocket. Hereby, we have identified a region that can be scrutinized to achieve selectivity for nicotinic receptor subtypes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.008
• 作为产物：
  描述：

  苯乙醛 、 8-Azabicyclo[3.2.1]octan-3-ol, benzoate (ester), endo- 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 3α-benzoyloxy-8-phenetyl-8-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Structure-based design, synthesis and structure–activity relationships of dibenzosuberyl- and benzoate-substituted tropines as ligands for acetylcholine-binding protein

  摘要：

  Using structure-based optimization procedures on in silico hits, dibenzosuberyl- and benzoate substituted tropines were designed as ligands for acetylcholine-binding protein (AChBP). This protein is a homolog to the ligand binding domain of the nicotinic acetylcholine receptor (nAChR). Distinct SAR is observed between two AChBP species variants and between the alpha 7 and alpha 4 beta 2 nAChR subtype. The AChBP species differences are indicative of a difference in accessibility of a ligand-inducible subpocket. Hereby, we have identified a region that can be scrutinized to achieve selectivity for nicotinic receptor subtypes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.008

文献信息

• Structure-based design, synthesis and structure–activity relationships of dibenzosuberyl- and benzoate-substituted tropines as ligands for acetylcholine-binding protein
  作者：Ewald Edink、Atilla Akdemir、Chimed Jansen、René van Elk、Obbe Zuiderveld、Frans J.J. de Kanter、Jacqueline E. van Muijlwijk-Koezen、August B. Smit、Rob Leurs、Iwan J.P. de Esch

  DOI：10.1016/j.bmcl.2011.12.008

  日期：2012.2

  Using structure-based optimization procedures on in silico hits, dibenzosuberyl- and benzoate substituted tropines were designed as ligands for acetylcholine-binding protein (AChBP). This protein is a homolog to the ligand binding domain of the nicotinic acetylcholine receptor (nAChR). Distinct SAR is observed between two AChBP species variants and between the alpha 7 and alpha 4 beta 2 nAChR subtype. The AChBP species differences are indicative of a difference in accessibility of a ligand-inducible subpocket. Hereby, we have identified a region that can be scrutinized to achieve selectivity for nicotinic receptor subtypes. (C) 2011 Elsevier Ltd. All rights reserved.