11-(2-butenyloxy)-N-propylnoraporphine | 1206545-64-3

• 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: 11-(2-butenyloxy)-N-propylnoraporphine
• CAS: 1206545-64-3
• 化学式: C₂₃H₂₇NO
• 分子量: 333.473
• InChiKey: VRGMZUXQIPKQOS-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  11-(2-butenyloxy)-N-propylnoraporphine 以 N,N-二乙基苯胺 为溶剂， 反应 1.5h， 以90%的产率得到10-(1-buten-3-yl)-11-hydroxy-N-propylnoraporphine
  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-(2-butynyloxy)-N-propylnoraporphine 在 喹啉 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以90%的产率得到11-(2-butenyloxy)-N-propylnoraporphine
  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