R(-)-11-Hydroxy-N-ethylnoraporphine | 794458-06-3

• 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: R(-)-11-Hydroxy-N-ethylnoraporphine
• 英文别名: R(-)-N-ethyl-11-hydroxynoraporphine；(6aR)-6-ethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol
• CAS: 794458-06-3
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: DWFDEIIDRXSKCU-OAHLLOKOSA-N

物化性质

• 沸点：
  444.1±33.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  R(-)-11-Hydroxy-N-ethylnoraporphine 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 R(-)-N-ethyl-11-hydroxynoraporphine hydrochloride
  参考文献：
  名称：

  [EN] R(-)-11-HYDROXYAPORPHINE DERIVATIVES AND USES THEREOF
  [FR] DERIVES DE R(20051222GAO Y ET AL: "Synthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine.", J MED CHEM., vol. 31, 1988, pages 1392 - 1396, XP002992383GAO Y ET ALSynthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine.J MED CHEM.19883113921396XXGRANCHELLI FE ET AL: "Aporphines. 23. Normorphothebaine derivatives: Synthesis of an aporphine nitrogen mustard.", J ORG CHEM., vol. 42, 1977, pages 2014 - 2017, XP002992384GRANCHELLI FE ET ALAporphines. 23. Normorphothebaine derivatives: Synthesis of an aporphine nitrogen mustard.J ORG CHEM.19774220142017XX

  摘要：

  公开号：

  WO2005099702A3
• 作为产物：
  描述：

  4,5α-epoxy-17-methyl-morphin-7-ene-3,6α-diol 在 palladium diacetate 甲酸 、 甲烷磺酸 、 碳酸氢钠 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 126.5h， 生成 R(-)-11-Hydroxy-N-ethylnoraporphine
  参考文献：
  名称：

  [EN] R(-)-11-HYDROXYAPORPHINE DERIVATIVES AND USES THEREOF
  [FR] DERIVES DE R(20051222GAO Y ET AL: "Synthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine.", J MED CHEM., vol. 31, 1988, pages 1392 - 1396, XP002992383GAO Y ET ALSynthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine.J MED CHEM.19883113921396XXGRANCHELLI FE ET AL: "Aporphines. 23. Normorphothebaine derivatives: Synthesis of an aporphine nitrogen mustard.", J ORG CHEM., vol. 42, 1977, pages 2014 - 2017, XP002992384GRANCHELLI FE ET ALAporphines. 23. Normorphothebaine derivatives: Synthesis of an aporphine nitrogen mustard.J ORG CHEM.19774220142017XX

  摘要：

  公开号：

  WO2005099702A3

文献信息

• R(-)-11-hydroxyaporphine derivatives and uses thereof
  申请人：Neumeyer L. John

  公开号：US20060040900A1

  公开（公告）日：2006-02-23

  The invention features derivatives of R(—)-11-hydroxyaporphines and methods of treating Parkinson's disease, sexual dysfunction, and depressive disorders therewith.

  本发明的特点是 R(-)-11-羟基阿扑啡的衍生物以及用其治疗帕金森病、性功能障碍和抑郁障碍的方法。
• Synthesis and neuropharmacological evaluation of R(−)-N-alkyl-11-hydroxynoraporphines and their esters
  作者：Csaba Csutoras、Ao Zhang、Kehong Zhang、Nora S. Kula、Ross J. Baldessarini、John L. Neumeyer

  DOI：10.1016/j.bmc.2004.04.029

  日期：2004.7

  We synthesized several N-substituted-11-hydroxynoraporphines and their esters of varying chain length, evaluated their binding affinity at dopamine (DA) receptor sites in rat caudate-putamen membranes, and quantified their effects on motor activity in normal adult male rats. The 11-hydroxyaporphines showed similar neuropharmacological properties to the corresponding 10,11-catecholaporphines. At moderate doses, their esters proved to have more prolonged behavioral actions and superior oral bioavailability. (C) 2004 Elsevier Ltd. All rights reserved.
• US7648995B2
  申请人：——

  公开号：US7648995B2

  公开（公告）日：2010-01-19
• US8063060B2
  申请人：——

  公开号：US8063060B2

  公开（公告）日：2011-11-22
• [EN] R(-)-11-HYDROXYAPORPHINE DERIVATIVES AND USES THEREOF<br/>[FR] DERIVES DE R(<supplemental>20051222</supplemental>GAO Y ET AL: "Synthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine.", J MED CHEM., vol. 31, 1988, pages 1392 - 1396, XP002992383GAO Y ET ALSynthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine.J MED CHEM.19883113921396XXGRANCHELLI FE ET AL: "Aporphines. 23. Normorphothebaine derivatives: Synthesis of an aporphine nitrogen mustard.", J ORG CHEM., vol. 42, 1977, pages 2014 - 2017, XP002992384GRANCHELLI FE ET ALAporphines. 23. Normorphothebaine derivatives: Synthesis of an aporphine nitrogen mustard.J ORG CHEM.19774220142017XX
  申请人：MCLEAN HOSPITAL CORP

  公开号：WO2005099702A3

  公开（公告）日：2005-12-22