8β-<(3,5-dioxo-4-phenylpiperazin-1-yl)methyl>-9,10-didehydro-6-methylergoline | 131816-90-5

• 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-phenylpiperazin-1-yl)methyl>-9,10-didehydro-6-methylergoline
• 英文别名: 4-[[(6aR,9S)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]methyl]-1-phenylpiperazine-2,6-dione
• CAS: 131816-90-5
• 化学式: C₂₆H₂₆N₄O₂
• 分子量: 426.518
• InChiKey: ILBJJSHICSZOET-UZUQRXQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8β-<(3,5-dioxo-4-phenylpiperazin-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 4-((6aR,9S,10aS)-7-Methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl)-1-phenyl-piperazine-2,6-dione 、 8β-<(3,5-dioxo-4-phenylpiperazin-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 氢氧化钾 、 N,N'-羰基二咪唑 作用下， 以 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.25h， 生成 8β-<(3,5-dioxo-4-phenylpiperazin-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

• ANTIEMESIS ERGOLINE DERIVATIVES
  申请人：FARMITALIA CARLO ERBA S.r.l.

  公开号：EP0418327B1

  公开（公告）日：1993-05-26
• US5202325A
  申请人：——

  公开号：US5202325A

  公开（公告）日：1993-04-13
• 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.