8β-<(3,5-dioxo-4-aminopiperazin-1-yl)methyl>-9,10-didehydro-6-methylergoline | 107052-58-4

• 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: 8β-<(3,5-dioxo-4-aminopiperazin-1-yl)methyl>-9,10-didehydro-6-methylergoline
• 英文别名: 6-Methyl-9,10-didehydro-8β-(3,5-dioxo-4-amino-piperazin-1-ylmethyl)-ergoline；4-[[(6aR,9S)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]methyl]-1-aminopiperazine-2,6-dione
• CAS: 107052-58-4
• 化学式: C₂₀H₂₃N₅O₂
• 分子量: 365.435
• InChiKey: JECYKSDGHSWHDA-SJKOYZFVSA-N

物化性质

• 沸点：
  610.3±65.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  85.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8β-<(3,5-dioxo-4-aminopiperazin-1-yl)methyl>-9,10-didehydro-6-methylergoline 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 8β-<(3,5-dioxo-4-aminopiperazin-1-yl)methyl>-6-methylergoline
  参考文献：
  名称：

  D1 Agonist and/or D2 antagonist dopamine receptor properties of a series of ergoline derivatives: a structure–activity study

  摘要：

  A series of (3,5-dioxopiperazin-1-yl)ergoline derivatives has been synthesised and evaluated in vitro and in vivo for their dopaminergic D-1 and D-2 components. The structural contributions to the pharmacological profile of the ergoline skeleton, its substituents on positions 1, 2, 6, 9, and the 3,5-dioxopiperazin-1-yl portion of the molecule were examined. Structure-activity relationships within this series suggested that substitution on the ergoline skeleton in position 1 or 2 and on the 3,5-dioxopiperazin-4-nitrogen generated compounds with a spectrum of dopamine agonistic/antagonistic activity sensitive to both the nature and position of substituents. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80045-2
• 作为产物：
  描述：

  lysergamine 在 potassium carbonate 、 一水合肼 、 苯酚 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 8β-<(3,5-dioxo-4-aminopiperazin-1-yl)methyl>-9,10-didehydro-6-methylergoline
  参考文献：
  名称：

  D1 Agonist and/or D2 antagonist dopamine receptor properties of a series of ergoline derivatives: a structure–activity study

  摘要：

  A series of (3,5-dioxopiperazin-1-yl)ergoline derivatives has been synthesised and evaluated in vitro and in vivo for their dopaminergic D-1 and D-2 components. The structural contributions to the pharmacological profile of the ergoline skeleton, its substituents on positions 1, 2, 6, 9, and the 3,5-dioxopiperazin-1-yl portion of the molecule were examined. Structure-activity relationships within this series suggested that substitution on the ergoline skeleton in position 1 or 2 and on the 3,5-dioxopiperazin-4-nitrogen generated compounds with a spectrum of dopamine agonistic/antagonistic activity sensitive to both the nature and position of substituents. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80045-2

文献信息

• Piperazin-1-yl-ergoline derivatives, process for preparing them and pharmaceutical compositions containing them
  申请人：FARMITALIA CARLO ERBA S.r.l.

  公开号：EP0197241B1

  公开（公告）日：1989-12-27
• US4728649A
  申请人：——

  公开号：US4728649A

  公开（公告）日：1988-03-01
• D1 Agonist and/or D2 antagonist dopamine receptor properties of a series of ergoline derivatives: a structure–activity study
  作者：Sergio Mantegani、Emanuele Arlandini、Tiziano Bandiera、Daniela Borghi、Enzo Brambilla、Carla Caccia、Maria Antonietta Cervini、Paolo Cremonesi、Robert Albert McArthur、Gabriella Traquandi、Mario Varasi

  DOI：10.1016/s0223-5234(99)80045-2

  日期：1999.2

  A series of (3,5-dioxopiperazin-1-yl)ergoline derivatives has been synthesised and evaluated in vitro and in vivo for their dopaminergic D-1 and D-2 components. The structural contributions to the pharmacological profile of the ergoline skeleton, its substituents on positions 1, 2, 6, 9, and the 3,5-dioxopiperazin-1-yl portion of the molecule were examined. Structure-activity relationships within this series suggested that substitution on the ergoline skeleton in position 1 or 2 and on the 3,5-dioxopiperazin-4-nitrogen generated compounds with a spectrum of dopamine agonistic/antagonistic activity sensitive to both the nature and position of substituents. (C) Elsevier, Paris.