epi-cyanolupinane | 38763-63-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: epi-cyanolupinane
• 英文别名: ω-epi-cyanolupinane；Epi-Cyan-Lupinan；((9aR)-(9ar)-octahydro-quinolizin-1c-yl)-acetonitrile；((9aR)-(9ar)-Octahydro-chinolizin-1c-yl)-acetonitril；2-[(1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]acetonitrile
• CAS: 38763-63-2
• 化学式: C₁₁H₁₈N₂
• 分子量: 178.277
• InChiKey: OIQLDCGCWJGORH-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  epi-cyanolupinane 在 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 反应 22.17h， 生成
  参考文献：
  名称：

  2-Phenyl-3-(quinolizidin-1-yl)-5-substituted indoles as platelet antiaggregating agents

  摘要：

  A set of ten 2-phenyl-3-(quinolizidin-1-yl)-5-substituted indoles was prepared through the Fischer cyclization of lupinyl- and epi-lupinylphenylketone 4-substituted phenylhydrazones. Compounds were tested for antiaggregating activity on human platelets activated by adenosine diphosphate (ADP), collagen and adrenaline. At 2.5 x 10(-4) M concentration most compounds strongly inhibited the aggregation induced by all the agonists considered and many of them still displayed good activity at 0.625 x 10(-4) M concentration. The least active (1c) and one of the most active (1d) compounds were also tested for antiaggregating activity on rabbit platelets activated by ADP, PAF and sodium arachidonate. Both the compounds were active against ADP and PAF, but only 1d inhibited the arachidonate-induced aggregation (100% at 8 x 10(-6) M concentration) and increased the bleeding time in mice. The same compounds were subjected to a general pharmacological screening and found to display several activities; of particular interest was the dose dependent reduction of serum cholesterol and heparin precipitating betalipoproteins in hypercholesterolemic mice exerted by 1c, which was still significant at the oral dose of 10 mg/kg.

  DOI：

  10.1016/j.farmac.2003.11.009
• 作为产物：
  描述：

  1-表羽扇豆碱 在 氯化亚砜 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 生成 epi-cyanolupinane
  参考文献：
  名称：

  2-Phenyl-3-(quinolizidin-1-yl)-5-substituted indoles as platelet antiaggregating agents

  摘要：

  A set of ten 2-phenyl-3-(quinolizidin-1-yl)-5-substituted indoles was prepared through the Fischer cyclization of lupinyl- and epi-lupinylphenylketone 4-substituted phenylhydrazones. Compounds were tested for antiaggregating activity on human platelets activated by adenosine diphosphate (ADP), collagen and adrenaline. At 2.5 x 10(-4) M concentration most compounds strongly inhibited the aggregation induced by all the agonists considered and many of them still displayed good activity at 0.625 x 10(-4) M concentration. The least active (1c) and one of the most active (1d) compounds were also tested for antiaggregating activity on rabbit platelets activated by ADP, PAF and sodium arachidonate. Both the compounds were active against ADP and PAF, but only 1d inhibited the arachidonate-induced aggregation (100% at 8 x 10(-6) M concentration) and increased the bleeding time in mice. The same compounds were subjected to a general pharmacological screening and found to display several activities; of particular interest was the dose dependent reduction of serum cholesterol and heparin precipitating betalipoproteins in hypercholesterolemic mice exerted by 1c, which was still significant at the oral dose of 10 mg/kg.

  DOI：

  10.1016/j.farmac.2003.11.009

文献信息

• 603. Syntheses from lupinine
  作者：G. R. Clemo、J. Rudinger

  DOI：10.1039/jr9510002714

  日期：——
• Sparatore, Anna; Novelli, Federica; Sparatore, Fabio, Medicinal Chemistry Research, 2002, vol. 11, # 1, p. 1 - 11
  作者：Sparatore, Anna、Novelli, Federica、Sparatore, Fabio

  DOI：——

  日期：——