(6aR,9R,10aR)-N-cyclohexyl-7-methyl-4-propyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-carboxamide | 123700-89-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: (6aR,9R,10aR)-N-cyclohexyl-7-methyl-4-propyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
• CAS: 123700-89-0
• 化学式: C₂₅H₃₅N₃O
• 分子量: 393.572
• InChiKey: DZOVEWIGQBAVLZ-JMUQELJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (6aR,9R,10aR)-7-methyl-4-propyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid 、 环己胺 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (6aR,9R,10aR)-N-cyclohexyl-7-methyl-4-propyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
  参考文献：
  名称：

  (8.beta.)-6-Methylergoline amide derivatives as serotonin antagonists: N1-substituent effects on vascular 5HT2 receptor activity

  摘要：

  A series of (8 beta)-6-methylergoline amide derivatives was synthesized with various alkyl substituents in the N1-position in order to evaluate their effectiveness in blocking vascular 5HT2 receptors. The influence of both the N1 substituent and amide derivative proved to be of great importance on binding affinities to vascular 5HT2 receptors. Within each series of amides, however, maximum affinity was achieved with an N1-isopropyl substituent (14, 18, 26, 38, and 41; all with 2.7-50 times greater affinity than their N1-H analogues), with the exception of two cases (22 and 37) in the cyclohexylamide derivatives wherein N1-methyl equalled the isopropyl in potency. Other than these exceptions, affinities followed the pattern of H less than Me less than Et less than iPr, with potencies falling off with larger alkyl substituents.

  DOI：

  10.1021/jm00164a029

文献信息

• (8.beta.)-6-Methylergoline amide derivatives as serotonin antagonists: N1-substituent effects on vascular 5HT2 receptor activity
  作者：Jerry W. Misner、William L. Garbrecht、Gifford Marzoni、Kathleen R. Whitten、Marlene L. Cohen

  DOI：10.1021/jm00164a029

  日期：1990.2

  A series of (8 beta)-6-methylergoline amide derivatives was synthesized with various alkyl substituents in the N1-position in order to evaluate their effectiveness in blocking vascular 5HT2 receptors. The influence of both the N1 substituent and amide derivative proved to be of great importance on binding affinities to vascular 5HT2 receptors. Within each series of amides, however, maximum affinity was achieved with an N1-isopropyl substituent (14, 18, 26, 38, and 41; all with 2.7-50 times greater affinity than their N1-H analogues), with the exception of two cases (22 and 37) in the cyclohexylamide derivatives wherein N1-methyl equalled the isopropyl in potency. Other than these exceptions, affinities followed the pattern of H less than Me less than Et less than iPr, with potencies falling off with larger alkyl substituents.