(+/-)-11-Hydroxy-N-propylnoraporphine | 79640-92-9

• 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-Hydroxy-N-propylnoraporphine
• 英文别名: (+/-)-11-hydroxy-N-n-propylnoraporphine；(6aRS)-11-hydroxy-N-propylnoraporphine；11-hydroxy-N-n-propylnoraporphine；11-hydroxy-N-propylnoraporphine；6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol；11-Hydroxy-N-n-propylnoraporphin；6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol
• CAS: 79640-92-9
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: WZJSIHGOLMMBAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  (+/-)-11-Hydroxy-N-propylnoraporphine 在 吡啶 、 ammonium hydroxide 、 四(三苯基膦)钯 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (6aRS)-11-(aminomethyl)-N-n-propylnoraporphine
  参考文献：
  名称：

  Identification of N-Propylnoraporphin-11-yl 5-(1,2-Dithiolan-3-yl)pentanoate as a New Anti-Parkinson's Agent Possessing a Dopamine D₂ and Serotonin 5-HT_1A Dual-Agonist Profile

  摘要：

  A series of new aporphine analogues (aporlogues) were synthesized bearing a C-, N-, or O-linkage at the C11 position. Lipoic ester (-)-15 was identified as a full agonist at the dopamine D-2 and serotonin 5-HT1A receptors with K-i values of 174 and 66 nM, respectively. It elicited antiparkinsonian action on Parkinsin's disease (PD) rats with minor dyskinesia. Chronic use of (-)-15 reduced L-DOPA-induced dyskinesia (LID) without attenuating the antiparkinsonian effect. These results suggest that 5-HT1A and D-2 dual-receptor agonist (-)-15 may present a novel candidate drug in the treatment of PD and LID.

  DOI：

  10.1021/jm200347t

文献信息

• Aporphines XXVI: GLC and mass spectrometric properties of trifluoroacetyl derivatives of N-methyl-, N-propyl-, and noraporphines
  作者：J.F. Green、G.N. Jham、J.L. Neumeyer、Paul Vouros

  DOI：10.1002/jps.2600690819

  日期：1980.8

  O-trifluoroacetyl and N,O-trifluoroacetyl derivatives of a series of aporphine and noraporphine alkaloids were prepared, and their GLC and mass spectrometric characteristics were determined. The positional isomers apocodeine and isoapocodeine were resolved chromatographically as their trifluoroacetyl derivatives, and their mass spectra were distinctly different. Mass spectrometry fragmentation processes

  制备了一系列阿菲啡碱和诺拉啡碱生物碱的O-三氟乙酰基和N，O-三氟乙酰基衍生物，并测定了它们的GLC和质谱特性。色谱分离出位置异构体apocodeine和isooapocodeine，为三氟乙酰基衍生物，其质谱图明显不同。观察到非rapophphines的N-三氟乙酰基衍生物特有的质谱裂解过程。给出了在各种化合物的质谱图中形成主要离子的合理机理。
• R(-)-2-METHOXY-11-HYDROXYAPORPHINE AND DERIVATIVES THEREOF
  申请人：Neumeyer John L.

  公开号：US20110034446A1

  公开（公告）日：2011-02-10

  The invention features derivatives of R(−)-2-methoxy-11-hydroxyaporphines and methods of treating Parkinson's disease, sexual dysfunction, and depressive disorders therewith.

  这项发明涉及R（-）-2-甲氧基-11-羟基阿品啡衍生物及其用于治疗帕金森病、性功能障碍和抑郁症的方法。
• 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。
• Further SAR study on 11-O-substituted aporphine analogues: Identification of highly potent dopamine D3 receptor ligands
  作者：Na Ye、QianQian Wu、Liyuan Zhu、Longtai Zheng、Bo Gao、Xuechu Zhen、Ao Zhang

  DOI：10.1016/j.bmc.2011.01.053

  日期：2011.3

  A series of new aporphine analogues (aporlogues) were prepared from appropriate aporphine precursors and arylpiperazines using the Click reaction protocol. These compounds displayed good to high affinity at the D-3 receptor, low or no affinity at the D-1 and D-2 receptors. Compounds 7f and 11c stood out as the most potent at the D-3 receptor among our newly synthesized aporlogues with K-i values of 2.67 and 1.14 nM, respectively. Further assay at the 5-HT1A receptor revealed that aporlogues 7f and 11c also showed high affinity at this receptor with K-i values of 9.68 and 7.59 nM, respectively. They were 3.6- and 6.6-fold more potent at the D-3 over 5-HT1A receptors. Such D-3/5-HT1A dual property of these compounds may be useful in the treatment of several brain disorders. (C) 2011 Elsevier Ltd. All rights reserved.
• R(-)-11-HYDROXYAPORPHINE DERIVATIVES AND USES THEREOF
  申请人：THE McLEAN HOSPITAL CORPORATION

  公开号：EP1737458A2

  公开（公告）日：2007-01-03