(R)-11-(2-Hydroxy-ethoxy)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol | 1056550-00-5

• 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)-11-(2-Hydroxy-ethoxy)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol
• 英文别名: (6aR)-11-(2-hydroxyethoxy)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol
• CAS: 1056550-00-5
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: FMNUYUVZQXAOTK-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 Pd/C 、 ammonium acetate 、 magnesium 作用下， 生成 (R)-11-(2-Hydroxy-ethoxy)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol
  参考文献：
  名称：

  Synthesis and binding studies of 2-O- and 11-O-substituted N-alkylnoraporphines

  摘要：

  We synthesized several novel 2-O- or 11-O-substituted N-alkylnoraporphines and assessed their affinities at dopamine D-1 and D-2, and serotonin 5-HT1A receptors in rat forebrain tissue. Tested compounds displayed moderate to high affinities to D-2 receptors but low affinities to D-1 and 5HT(1A) receptors. The findings accord with previous evidence of a lipophilic cavity on the surface of the D-2 receptor to accommodate N-alkyl moieties of aporphines. The most D-2- potent (K-i = 97 nM) and selective novel agent (> 100-fold vs. D-1 and 5-HT1A sites) was R(-)-2-(2-hydroxyethoxy)-11-hydroxy-N-n-propylnoraporphine (compound 11). (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.016

文献信息

• Synthesis and binding studies of 2-O- and 11-O-substituted N-alkylnoraporphines
  作者：Yu-Gui Si、Matthew P. Gardner、Frank I. Tarazi、Ross J. Baldessarini、John L. Neumeyer

  DOI：10.1016/j.bmcl.2008.06.016

  日期：2008.7

  We synthesized several novel 2-O- or 11-O-substituted N-alkylnoraporphines and assessed their affinities at dopamine D-1 and D-2, and serotonin 5-HT1A receptors in rat forebrain tissue. Tested compounds displayed moderate to high affinities to D-2 receptors but low affinities to D-1 and 5HT(1A) receptors. The findings accord with previous evidence of a lipophilic cavity on the surface of the D-2 receptor to accommodate N-alkyl moieties of aporphines. The most D-2- potent (K-i = 97 nM) and selective novel agent (> 100-fold vs. D-1 and 5-HT1A sites) was R(-)-2-(2-hydroxyethoxy)-11-hydroxy-N-n-propylnoraporphine (compound 11). (c) 2008 Elsevier Ltd. All rights reserved.