(2S,11bS)-3'-ethyl-9,10-dimethoxyspiro[1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine-2,5'-1,3-oxazolidine]-2'-one | 86457-45-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (2S,11bS)-3'-ethyl-9,10-dimethoxyspiro[1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine-2,5'-1,3-oxazolidine]-2'-one
• CAS: 86457-45-6
• 化学式: C₁₉H₂₆N₂O₄
• 分子量: 346.426
• InChiKey: JTVUSYASBKDDGI-KXBFYZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  9,10-dimethoxyspiro[1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine-2,2'-oxirane] 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 生成 (2S,11bS)-3'-ethyl-9,10-dimethoxyspiro[1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine-2,5'-1,3-oxazolidine]-2'-one
  参考文献：
  名称：

  Synthesis and antihypertensive activity of a series of spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one]s

  摘要：

  The 2R*,11bS* and 2S*,11bS* diastereoisomers of the spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2, 5'-oxazolidin-2'-one] system were prepared by stereoselective methods. Evaluation of these compounds for antihypertensive activity by oral administration to the spontaneously hypertensive rat showed the 2S*,11bS* series was the more potent. Within that series it was found that small alkyl substituents at positions 3 and 4' enhanced antihypertensive activity and that methoxyl substitution at positions 9 and 10 was optimal. (2S,3S,11bS)-Spiro-[2-ethyl-9,10-dimethoxy-1,3,4,6,7, 11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one] [(-)-9e] was one of the most efficacious compounds of this series, while its antipode, (+)-9e, was inactive. Selected compounds in this series were shown to be alpha-adrenoceptor antagonists.

  DOI：

  10.1021/jm00364a013