3β-benzoyloxy-8-(2-(3,5-dihydroxyphenyl)-2-oxoethyl)-8-azabicyclo[3.2.1]octane | 1360460-74-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 3β-benzoyloxy-8-(2-(3,5-dihydroxyphenyl)-2-oxoethyl)-8-azabicyclo[3.2.1]octane
• CAS: 1360460-74-7
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: XCZOLMUIUBTIRC-YRWFTTLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  87.07
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3β-benzoyloxy-8-(2-(3,5-dihydroxyphenyl)-2-oxoethyl)-8-azabicyclo[3.2.1]octane 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以39%的产率得到3β-benzoyloxy-8-(2-hydroxy-2-(3,5-dihydroxyphenyl)ethyl)-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
• 作为产物：
  描述：

  endo-benzoic acid 8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester 在 N,N-二异丙基乙胺 作用下， 以 甲醇 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 41.0h， 生成 3β-benzoyloxy-8-(2-(3,5-dihydroxyphenyl)-2-oxoethyl)-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