(R)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-yl trifluoromethanesulfonate | 1310743-31-7

• 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)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-yl trifluoromethanesulfonate
• CAS: 1310743-31-7
• 化学式: C₂₀H₂₀F₃NO₃S
• 分子量: 411.445
• InChiKey: JDMOZDAVYGQTSY-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  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 、 4-二甲氨基吡啶 、 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (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：

  三氟甲磺酸酐 、 (R)-(-)-11-hydroxy-N-n-propylnoraporphine 在 吡啶 作用下， 以98%的产率得到(R)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-yl trifluoromethanesulfonate
  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