2-[Carbamoylmethyl-((6aR,9S,10R,10aR)-10-hydroxy-7-methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl)-amino]-acetamide | 1027252-60-3

• 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: 2-[Carbamoylmethyl-((6aR,9S,10R,10aR)-10-hydroxy-7-methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl)-amino]-acetamide
• 英文别名: 2-[[(6aR,9S,10R,10aR)-10-hydroxy-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]methyl-(2-amino-2-oxoethyl)amino]acetamide
• CAS: 1027252-60-3
• 化学式: C₂₀H₂₇N₅O₃
• 分子量: 385.466
• InChiKey: KHIJJFGGEDMJBX-DDAIWRKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[Carbamoylmethyl-((6aR,9S,10R,10aR)-10-hydroxy-7-methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl)-amino]-acetamide 在 苯酚 作用下， 生成 8β-(3,5-dioxopiperazin-1-ylmethyl)-9α-hydroxy-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：

  (5R,8R)-6-methyl-8β-hydroxymethyl-9α-hydroxyergoline 在 氨 、 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 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 2-[Carbamoylmethyl-((6aR,9S,10R,10aR)-10-hydroxy-7-methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl)-amino]-acetamide
  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

• 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.