8β-(3,5-dioxopiperazin-1-ylmethyl)-9,10-didehydro-1,6-dimethylergoline | 136670-05-8

• 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-dioxopiperazin-1-ylmethyl)-9,10-didehydro-1,6-dimethylergoline
• 英文别名: 4-[[(6aR,9S)-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinolin-9-yl]methyl]piperazine-2,6-dione
• CAS: 136670-05-8
• 化学式: C₂₁H₂₄N₄O₂
• 分子量: 364.447
• InChiKey: YXFYLDTZQCOFFD-FZKQIMNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8β-(3,5-dioxopiperazin-1-ylmethyl)-9,10-didehydro-1,6-dimethylergoline 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 4-((6aR,9S,10aS)-4,7-Dimethyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl)-piperazine-2,6-dione 、 8β-(3,5-dioxopiperazin-1-ylmethyl)-1,6-dimethylergoline
  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：

  1-Methyllysergol 在 氨 、 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 、 苯酚 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 8β-(3,5-dioxopiperazin-1-ylmethyl)-9,10-didehydro-1,6-dimethylergoline
  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：EP0371246A1

  公开（公告）日：1990-06-06

  Compounds of the formula I wherein n is 1 or 2, R₁ represents a hydrogen atom or a C₁-C₄ alkyl group, R₂ represents a hydrogen atom and R₃ represents a hydrogen atom or a hydroxy group or R₂ and R₃ together represent a chemical bond, R₄ represents a hydrogen atom, or a phenyl or C₁-C₄ alkyl group, R₅ represents a C₁-C₄ alkyl group or an allyl group and R₆ represents a hydrogen or halogen atom, and the pharmaceutically acceptable salt thereof, are useful for the manufacture of a pharmaceutical composition useful in the treatment of emesis.

  式 I 的化合物 其中 n 为 1 或 2，R₁ 代表氢原子或 C₁-C₄ 烷基，R₂ 代表氢原子，R₃ 代表氢原子或羟基或 R₂ 和 R₃ 共同代表化学键，R₄ 代表氢原子、或苯基或 C₁-C₄烷基，R₅代表 C₁-C₄烷基或烯丙基，R₆代表氢原子或卤素原子，及其药学上可接受的盐，可用于制造治疗呃逆的药物组合物。
• 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.