rac-8β-benzo[1,3]dioxol-5-yl-6-methyl-9,10-didehydro-(3β)-2,3-dihydro-ergoline | 63460-53-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: rac-8β-benzo[1,3]dioxol-5-yl-6-methyl-9,10-didehydro-(3β)-2,3-dihydro-ergoline
• 英文别名: (5aS,6aR,9S)-9-(1,3-benzodioxol-5-yl)-7-methyl-5,5a,6,6a,8,9-hexahydro-4H-indolo[4,3-fg]quinoline
• CAS: 63460-53-7
• 化学式: C₂₂H₂₂N₂O₂
• 分子量: 346.429
• InChiKey: DWXWESOUQKEWHA-SPYBWZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  胡椒环 、 rac-6-methyl-9,10-didehydro-(3β)-2,3-dihydro-ergolin-8β-ol 在 三氟化硼乙醚 、 三氟乙酸 作用下， 以 苯 为溶剂， 生成 rac-8α-benzo[1,3]dioxol-5-yl-6-methyl-9,10-didehydro-(3β)-2,3-dihydro-ergoline 、 rac-8β-benzo[1,3]dioxol-5-yl-6-methyl-9,10-didehydro-(3β)-2,3-dihydro-ergoline
  参考文献：
  名称：

  Synthesis and biological activity of 8-arylergolines

  摘要：

  9,10-Didehydro-6-methyl-8beta-arylergolines 2, in which the carboxyl group of lysergic acid and isolysergic acid is replaced by various aryl groups, were prepared in two steps by alkylation of aromatic substrates with the tetracyclic allylic alcohol 3, followed by aromatization with MnO2. The new ergolines 2 have modest prolactin-inhibiting and rat antimuricidal activities and possess significant alpha-blocking and antiserotonin properties.

  DOI：

  10.1021/jm00218a025

文献信息

• Synthesis and biological activity of 8-arylergolines
  作者：Nicholas J. Bach、Edmund C. Kornfeld、Douglas E. Dorman

  DOI：10.1021/jm00218a025

  日期：1977.8

  9,10-Didehydro-6-methyl-8beta-arylergolines 2, in which the carboxyl group of lysergic acid and isolysergic acid is replaced by various aryl groups, were prepared in two steps by alkylation of aromatic substrates with the tetracyclic allylic alcohol 3, followed by aromatization with MnO2. The new ergolines 2 have modest prolactin-inhibiting and rat antimuricidal activities and possess significant alpha-blocking and antiserotonin properties.