(6aR)-11-amino-N-n-propylnoraporphine | 1310743-32-8

• 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: (6aR)-11-amino-N-n-propylnoraporphine
• 英文别名: (6aR)-11-amino-N-propylnoraporphine；SOMCL-171；(6aR)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-amine
• CAS: 1310743-32-8
• 化学式: C₁₉H₂₂N₂
• 分子量: 278.397
• InChiKey: LKVRAIZDZUXRII-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6aR)-11-amino-N-n-propylnoraporphine 、 丁酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到(6aR)-N-n-propylnoraporphin-11-yl butyramide
  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
• 作为产物：
  描述：

  (R)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-yl trifluoromethanesulfonate 在 二苯甲酮亚胺 、 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 、 盐酸羟胺 、 sodium acetate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以46%的产率得到(6aR)-11-amino-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

• Identification of <i>N</i>-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
  作者：Hai Zhang、Na Ye、Shanglin Zhou、Lin Guo、Longtai Zheng、Zhili Liu、Bo Gao、Xuechu Zhen、Ao Zhang

  DOI：10.1021/jm200347t

  日期：2011.7.14

  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.