3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-yloxy)-8-phenethyl-8-aza-bicyclo[3.2.1]octane | 47702-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-yloxy)-8-phenethyl-8-aza-bicyclo[3.2.1]octane
• 英文别名: 3α-((10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)oxy)-8α-phenetyl-8-azabicyclo[3.2.1]octane
• CAS: 47702-79-4
• 化学式: C₃₀H₃₃NO
• 分子量: 423.598
• InChiKey: KEGNCHJKYCGHJN-UQWUFBTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12.47
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-yloxy)-8-phenethyl-8-aza-bicyclo[3.2.1]octane 、 碘甲烷 以 甲苯 为溶剂， 以77 mg的产率得到3α-((10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)oxy)-8α-phenetyl-8-azabicyclo[3.2.1]octane methiodide
  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：

  3-tropanol 在 potassium permanganate 、 三乙酰氧基硼氢化钠 、 potassium hydroxide 作用下， 以 吡啶 、 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 5.0h， 生成 3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-yloxy)-8-phenethyl-8-aza-bicyclo[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.