9-[2-(1H-Indol-3-yl)-ethyl]-5-phenyl-1-oxa-4,9-diaza-spiro[5.5]undecan-3-one | 85151-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 9-[2-(1H-Indol-3-yl)-ethyl]-5-phenyl-1-oxa-4,9-diaza-spiro[5.5]undecan-3-one
• 英文别名: 9-[2-(1H-indol-3-yl)ethyl]-5-phenyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one
• CAS: 85151-29-7
• 化学式: C₂₄H₂₇N₃O₂
• 分子量: 389.497
• InChiKey: WIIUOCVJCVDAMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(2-溴乙基)吲哚 、 在 TEA 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以30%的产率得到9-[2-(1H-Indol-3-yl)-ethyl]-5-phenyl-1-oxa-4,9-diaza-spiro[5.5]undecan-3-one
  参考文献：
  名称：

  Antihypertensive 9-substituted 1-0xa-4,9-diazaspiro[5.5]undecan-3-ones

  摘要：

  Forty-one 9-substituted 1-oxa-4,9-diazaspiro[5.5]undecan-3-ones were prepared for antihypertensive screening in the spontaneously hypertensive rat (SHR). For the 9-(2-indol-3-ylethyl) series, the parent compound, 9-(2-indol-3-ylethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-3-one (21), was the most potent antihypertensive agent. Substitution of lower alkyl groups on the spirolactam ring gave compounds close in activity to 21, while substitution with large alkyl or aryl groups led to a significant decrease in activity. Ring-opened analogues of 21 that contained the same functionality were markedly less active. Several 1-oxa-4,9-diazaspiro[5.5]undecan-3-ones substituted at the 9 position with 1,4-benzodioxan-2-ylmethyl, 1,4-benzodioxan-2-ylhydroxyethyl, and 2-phenylethyl groups also demonstrated significant activity. Compound 21 was chosen for a detailed pharmacological evaluation. Its antihypertensive activity appears to be predominantly due to peripheral alpha 1-adrenoceptor blockade.

  DOI：

  10.1021/jm00360a013