(R)-(-)-2-methoxy-11-((4-fluorobenzyl)oxy)aporphine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: (R)-(-)-2-methoxy-11-((4-fluorobenzyl)oxy)aporphine
• 英文别名: (6aR)-11-[(4-fluorophenyl)methoxy]-2-methoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
• 化学式: C₂₅H₂₄FNO₂
• 分子量: 389.469
• InChiKey: TVOXJDSQQBHAKL-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-methoxy-11-((4-fluorobenzyl)oxy)aporphine 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (R)-(-)-2-methoxy-11-((4-fluorobenzyl)oxy)aporphine hydrochloride
  参考文献：
  名称：

  Identification of fluorinated (R)-(−)-aporphine derivatives as potent and selective ligands at serotonin 5-HT2C receptor

  摘要：

  A series of novel aporphine derivatives were synthesized for initial screening at the 5-HT2 receptor subtypes. Among them, Compounds 11a and 11b were identified as potent 5-HT2C hit ligands with high selectivity over other 5-HT2 receptor subtypes. Molecular docking study revealed that compounds 11a and 11b formed two key interactions with the binding site of 5-HT2C receptor, including a salt-bridge to D3.32 and a H-bond interaction with N6.55.

  DOI：

  10.1016/j.bmcl.2018.11.050
• 作为产物：
  描述：

  蒂巴因 在 甲烷磺酸 、 palladium on activated charcoal 、 ammonium acetate 、 L-Selectride 、 potassium carbonate 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (R)-(-)-2-methoxy-11-((4-fluorobenzyl)oxy)aporphine
  参考文献：
  名称：

  Identification of fluorinated (R)-(−)-aporphine derivatives as potent and selective ligands at serotonin 5-HT2C receptor

  摘要：

  A series of novel aporphine derivatives were synthesized for initial screening at the 5-HT2 receptor subtypes. Among them, Compounds 11a and 11b were identified as potent 5-HT2C hit ligands with high selectivity over other 5-HT2 receptor subtypes. Molecular docking study revealed that compounds 11a and 11b formed two key interactions with the binding site of 5-HT2C receptor, including a salt-bridge to D3.32 and a H-bond interaction with N6.55.

  DOI：

  10.1016/j.bmcl.2018.11.050

文献信息

• Identification of fluorinated (R)-(−)-aporphine derivatives as potent and selective ligands at serotonin 5-HT2C receptor
  作者：Yulong Xu、Anna W. Sromek、John L. Neumeyer

  DOI：10.1016/j.bmcl.2018.11.050

  日期：2019.1

  A series of novel aporphine derivatives were synthesized for initial screening at the 5-HT2 receptor subtypes. Among them, Compounds 11a and 11b were identified as potent 5-HT2C hit ligands with high selectivity over other 5-HT2 receptor subtypes. Molecular docking study revealed that compounds 11a and 11b formed two key interactions with the binding site of 5-HT2C receptor, including a salt-bridge to D3.32 and a H-bond interaction with N6.55.