(6aRS)-11-[5-(1,2-dithiolan-3-yl)pentyloxy]-N-n-propylnoraporphine | 1310743-29-3

• 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: (6aRS)-11-[5-(1,2-dithiolan-3-yl)pentyloxy]-N-n-propylnoraporphine
• 英文别名: (6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-yl) 5-(dithiolan-3-yl)pentanoate
• CAS: 1310743-29-3
• 化学式: C₂₇H₃₃NO₂S₂
• 分子量: 467.697
• InChiKey: JCKSBFDVTFRZJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  80.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6aRS)-11-[5-(1,2-dithiolan-3-yl)pentyloxy]-N-n-propylnoraporphine 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (6aRS)-11-[5-(1,2-dithiolan-3-yl)pentyloxy]-N-n-propylnoraporphine hydrochloride
  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：

  (+/-)-11-Hydroxy-N-propylnoraporphine 、 Thioctic acid 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78%的产率得到(6aRS)-11-[5-(1,2-dithiolan-3-yl)pentyloxy]-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.