3-acetoxy-8β-acetylthio-dihydromorphinone | 168644-35-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 3-acetoxy-8β-acetylthio-dihydromorphinone
• CAS: 168644-35-7
• 化学式: C₂₁H₂₃NO₅S
• 分子量: 401.483
• InChiKey: FTBACHGFACZRLR-XBPNULNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-acetoxy-8β-acetylthio-dihydromorphinone 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 8β-(5-nitro-2-pyridinesulfenyl)thio-dihydromorphine
  参考文献：
  名称：

  Ligand recognition in μ opioid receptor: experimentally based modeling of μ opioid receptor binding sites and their testing by ligand docking

  摘要：

  For three-dimensional understanding of the mechanisms that control potency and selectivity of the ligand binding at the atomic level, we have analysed opioid receptor-ligand interaction based on the receptor's 3D model. As a first step, we have constructed molecular models for the multiple opioid receptor subtypes using bacteriorhodopsin as a template. The S-activated dihydromorphine derivatives should serve as powerful tools in mapping the three-dimensional structure of the mu opioid receptor, including the nature of the agonist-mediated conformational change that permits G protein-coupling to 'second messenger' effector molecules, and in identifying specific ligand-binding contacts with the mu opioid receptor. The analyses of the interactions of some opioid ligands with the predicted ligand binding sites are consistent with the results of the affinity labeling experiments. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00219-2
• 作为产物：
  描述：

  O(3)-单乙酰吗啡 在 2,6-二甲基吡啶 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 3-acetoxy-8β-acetylthio-dihydromorphinone
  参考文献：
  名称：

  Ligand recognition in μ opioid receptor: experimentally based modeling of μ opioid receptor binding sites and their testing by ligand docking

  摘要：

  For three-dimensional understanding of the mechanisms that control potency and selectivity of the ligand binding at the atomic level, we have analysed opioid receptor-ligand interaction based on the receptor's 3D model. As a first step, we have constructed molecular models for the multiple opioid receptor subtypes using bacteriorhodopsin as a template. The S-activated dihydromorphine derivatives should serve as powerful tools in mapping the three-dimensional structure of the mu opioid receptor, including the nature of the agonist-mediated conformational change that permits G protein-coupling to 'second messenger' effector molecules, and in identifying specific ligand-binding contacts with the mu opioid receptor. The analyses of the interactions of some opioid ligands with the predicted ligand binding sites are consistent with the results of the affinity labeling experiments. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00219-2