2'-methyl-2',3'-dihydrofuro[m]aporphine | 1250264-58-4

• 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'-methyl-2',3'-dihydrofuro[m]aporphine
• 英文别名: (12R)-5,13-dimethyl-4-oxa-13-azapentacyclo[10.7.1.02,10.03,7.016,20]icosa-1(19),2(10),3(7),8,16(20),17-hexaene
• CAS: 1250264-58-4
• 化学式: C₂₀H₂₁NO
• 分子量: 291.393
• InChiKey: MSFBLSXHRFJARJ-RGUGMKFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2'-methyl-2',3'-dihydrofuro[m]aporphine 在 Chiracel OD column 作用下， 以 正己烷 、 二乙胺 、 异丙醇 为溶剂， 生成 (6aR,2'R)-2'-methyl-2',3'-dihydrofuro[m]aporphine 、 (6aR,2'S)-2'-methyl-2',3'-dihydrofuro[m]aporphine
  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：

  2'-methylfuro[m]aporphine 在 1% Pd/C 、 氢气 作用下， 生成 2'-methyl-2',3'-dihydrofuro[m]aporphine
  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.