ω-cyanolupinane | 5176-10-3

• 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: ω-cyanolupinane
• 英文别名: 2-[(1S,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]acetonitrile
• CAS: 5176-10-3
• 化学式: C₁₁H₁₈N₂
• 分子量: 178.277
• InChiKey: OIQLDCGCWJGORH-WDEREUQCSA-N

物化性质

• 沸点：
  305.3±15.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

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：

  ω-cyanolupinane 在 sodium hydroxide 、 盐酸羟胺 、 碘 、 magnesium 、 碘甲烷 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 7.5h， 生成 dilupinyl ketone oxime
  参考文献：
  名称：

  Sparatore; Boido; Sparatore, Il Farmaco, 1989, vol. 44, # 12, p. 1193 - 1203

  摘要：

  DOI：
• 作为产物：
  描述：

  羽扇豆宁 在 乙醇 、 三溴化磷 、 苯 作用下， 生成 ω-cyanolupinane
  参考文献：
  名称：

  603.羽扇豆碱的合成

  摘要：

  DOI：

  10.1039/jr9510002714

文献信息

• 1-(Arylalkyl)quinolizidine Derivatives and Thio-Isosteric Analogues as Ligands for Sigma Receptors
  作者：Anna Sparatore、Federica Novelli、Fabio Sparatore

  DOI：10.1002/hlca.200490055

  日期：2004.3

  congeners were synthesized (see 1–25) and tested for affinity to sigma 1 and sigma 2 receptor subtypes, by displacing [3H]- (+)-pentazocine and [3H]DTG from guinea pig brain and rat brain preparations, respectively. All compounds exhibited a good affinity for the σ1 subtype, with subnanomolar Ki values for the best of them, while only modest or poor affinity for the σ2 subtype was observed (Tables 1 and 2)

  一组的1-（芳基烷基）喹，电子等排thioanalogues，以及各种官能化同类物合成（参见1 - 25）和亲和力西格玛1和sigma 2受体亚型，测试通过置换[ 3 H] - （+） -喷他佐辛和[ 3 H] DTG分别来自豚鼠脑和大鼠脑制剂。所有的化合物显示了良好的亲合性为σ 1亚型，以亚纳摩尔ķ我为其中最好的值，而对于仅适度或亲和性差σ 2中观察到（亚型表1和2）。提出了一些构效关系。
• 2-Phenyl-3-(quinolizidin-1-yl)-5-substituted indoles as platelet antiaggregating agents
  作者：Marcella Ercoli、Lorenzo Mina、Caterina Canu Boido、Vito Boido、Fabio Sparatore、Ugo Armani、Antonietta Piana

  DOI：10.1016/j.farmac.2003.11.009

  日期：2004.2

  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.
• 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：——