(6aR,9R)-9-Methyl-7-propyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline | 114221-34-0

• 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)-9-Methyl-7-propyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline
• 英文别名: (6aR,9R)-9-methyl-7-propyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline
• CAS: 114221-34-0
• 化学式: C₁₈H₂₂N₂
• 分子量: 266.386
• InChiKey: WZNTUIITTOFVJK-SJKOYZFVSA-N

物化性质

• 沸点：
  444.6±40.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  19.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (6aR,9R)-9-Methyl-7-propyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 6.0h， 以7%的产率得到(3β,5β,8β)-9,10-didehydro-2,3-dihydro-8-methyl-6-propylergoline
  参考文献：
  名称：

  Ergolines as selective 5-HT1 agonists

  摘要：

  The synthesis and serotonin receptor subtype affinity of a series of ergolines are described. High selectivity for the 5-HT1 subtype was found with a number of 8-substituted (3 beta, 5 beta)-9,10-didehydro-6-methylergolines. The more potent and selective of these compounds increased the concentration of serotonin and decreased the concentration of 5-HIAA in rat brain and increased corticosterone concentration in rat serum. Oral administration of 13, (3 beta)-2,3-dihydrolysergine, produced long-lasting decreases in serotonin turnover. Compound 13 lacked substantial dopaminergic activity as measured by its effects on dopamine turnover in whole brain or striatum and its affinity for alpha-adrenergic binding sites was significantly less than for 5-HT1 binding sites. The increases in serum corticosterone concentrations produced by 13 were not blocked by the serotonin uptake inhibitor fluoxetine or by the serotonin synthesis inhibitor p-chlorophenylalanine, suggesting that 13 exerts its effects through direct stimulation of serotonin receptors.

  DOI：

  10.1021/jm00403a007
• 作为产物：
  描述：

  (5β,8β)-9,10-didehydro-8-methyl-6-cyanoergoline 在 potassium carbonate 、 溶剂黄146 、 锌 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 (6aR,9R)-9-Methyl-7-propyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline
  参考文献：
  名称：

  Ergolines as selective 5-HT1 agonists

  摘要：

  The synthesis and serotonin receptor subtype affinity of a series of ergolines are described. High selectivity for the 5-HT1 subtype was found with a number of 8-substituted (3 beta, 5 beta)-9,10-didehydro-6-methylergolines. The more potent and selective of these compounds increased the concentration of serotonin and decreased the concentration of 5-HIAA in rat brain and increased corticosterone concentration in rat serum. Oral administration of 13, (3 beta)-2,3-dihydrolysergine, produced long-lasting decreases in serotonin turnover. Compound 13 lacked substantial dopaminergic activity as measured by its effects on dopamine turnover in whole brain or striatum and its affinity for alpha-adrenergic binding sites was significantly less than for 5-HT1 binding sites. The increases in serum corticosterone concentrations produced by 13 were not blocked by the serotonin uptake inhibitor fluoxetine or by the serotonin synthesis inhibitor p-chlorophenylalanine, suggesting that 13 exerts its effects through direct stimulation of serotonin receptors.

  DOI：

  10.1021/jm00403a007

文献信息

• WARD, JOHN S.;FULLER, RAY W.;MERRITT, LEANDER;SNODDY, HAROLD D.;PASCHAL, +, J. MED. CHEM., 31,(1988) N 8, C. 1512-1519
  作者：WARD, JOHN S.、FULLER, RAY W.、MERRITT, LEANDER、SNODDY, HAROLD D.、PASCHAL, +

  DOI：——

  日期：——