2-methoxy-11-allyloxyaporphine | 1206545-55-2

• 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: 2-methoxy-11-allyloxyaporphine
• 英文别名: 2-Methoxy-11-allyloxy-N-methylaporphine；(6aR)-2-methoxy-6-methyl-11-prop-2-enoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
• CAS: 1206545-55-2
• 化学式: C₂₁H₂₃NO₂
• 分子量: 321.419
• InChiKey: DQHOPVHCOMQTNV-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methoxy-11-allyloxyaporphine 以 N,N-二乙基苯胺 为溶剂， 反应 1.5h， 以47%的产率得到2-methoxy-10-allyl-11-hydroxyaporphine
  参考文献：
  名称：

  Synthesis of Dihydrofuroaporphine Derivatives: Identification of a Potent and Selective Serotonin 5-HT_1A Receptor Agonist

  摘要：

  A series of new aporphine analogues were synthesized and pharmacologically evaluated. 11-Allyloxy-(17), 11-propargyloxy-(20), and dihydrofuro-(19) aporphines displayed the highest affinity at the 5-HT1A receptor with K-i values of 12.0, 14.0, and 6.7 nM, respectively. The high binding potential of the diastereomeric mixture of aporphine 19 was found residing in the cis-diastereomer (cis-19). [S-35]GTP gamma S function assays on 5-HT1A receptor indicated that aporphines 17 and 20 were partial agonists, while trans-19 behaved as a high efficacy full antagonist and cis-19 was a full agonist. The agonistic property of cis-19 at the 5-HT1A receptor was further confirmed in vitro and in vivo. This compound may be useful as a potential treatment for anxiety.

  DOI：

  10.1021/jm9015763
• 作为产物：
  描述：

  11-hydroxy-2-methoxyaporphine 、 3-溴丙烯 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以34%的产率得到2-methoxy-11-allyloxyaporphine
  参考文献：
  名称：

  Synthesis of Dihydrofuroaporphine Derivatives: Identification of a Potent and Selective Serotonin 5-HT_1A Receptor Agonist

  摘要：

  A series of new aporphine analogues were synthesized and pharmacologically evaluated. 11-Allyloxy-(17), 11-propargyloxy-(20), and dihydrofuro-(19) aporphines displayed the highest affinity at the 5-HT1A receptor with K-i values of 12.0, 14.0, and 6.7 nM, respectively. The high binding potential of the diastereomeric mixture of aporphine 19 was found residing in the cis-diastereomer (cis-19). [S-35]GTP gamma S function assays on 5-HT1A receptor indicated that aporphines 17 and 20 were partial agonists, while trans-19 behaved as a high efficacy full antagonist and cis-19 was a full agonist. The agonistic property of cis-19 at the 5-HT1A receptor was further confirmed in vitro and in vivo. This compound may be useful as a potential treatment for anxiety.

  DOI：

  10.1021/jm9015763

文献信息

• Synthesis of Dihydrofuroaporphine Derivatives: Identification of a Potent and Selective Serotonin 5-HT_1A Receptor Agonist
  作者：Zhili Liu、Hai Zhang、Na Ye、Jing Zhang、QianQian Wu、Peihua Sun、Linyong Li、Xuechu Zhen、Ao Zhang

  DOI：10.1021/jm9015763

  日期：2010.2.11

  A series of new aporphine analogues were synthesized and pharmacologically evaluated. 11-Allyloxy-(17), 11-propargyloxy-(20), and dihydrofuro-(19) aporphines displayed the highest affinity at the 5-HT1A receptor with K-i values of 12.0, 14.0, and 6.7 nM, respectively. The high binding potential of the diastereomeric mixture of aporphine 19 was found residing in the cis-diastereomer (cis-19). [S-35]GTP gamma S function assays on 5-HT1A receptor indicated that aporphines 17 and 20 were partial agonists, while trans-19 behaved as a high efficacy full antagonist and cis-19 was a full agonist. The agonistic property of cis-19 at the 5-HT1A receptor was further confirmed in vitro and in vivo. This compound may be useful as a potential treatment for anxiety.