8β-(3,5-dioxopiperazin-1-ylmethyl)-6-methylergoline

• 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)-6-methylergoline
• 英文别名: 6-methyl-8β-(3,5-dioxo-piperazin-1-ylmethyl)-ergoline；4-[[(6aR,9S,10aR)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]methyl]piperazine-2,6-dione
• 化学式: C₂₀H₂₄N₄O₂
• 分子量: 352.436
• InChiKey: GKGXKTYGQHBSPX-SRCQZFHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,6-哌嗪二酮 、 (5R,8R,10R)-6-methyl-8-ergolinylmethyl p-toluenesulfonate 在 potassium iodide 作用下， 以 N-甲基乙酰胺 、 二氯甲烷 为溶剂， 生成 8β-(3,5-dioxopiperazin-1-ylmethyl)-6-methylergoline
  参考文献：
  名称：

  3-oxo-piperazin-1-yl-ergolines exhibiting antidopaminergic activity

  摘要：

  该发明涉及具有一般式（I）的麦角酸衍生物：其中R=H，CH3；R1=H，卤素，CH3，苯硫醚，C1-C4烷硫基；R2=H，CH3O，R3=H或R2+R3=化学键；R4=C1-C4碳氢化合物；R5、R6、R8、R9独立地=H，C1-C4烷基，或R5、R8独立地=H，C1-C4烷基和R6+R9=CH2CH2，CH2CH2CH2；R7=H，C1-C4烷基，苯基，NR'R"；R'，R"独立地=H，C1-C4烷基，酰基或NR'R"=杂环；W=0，H2；n=0，1，2，及其药学上可接受的盐，这些化合物具有降压活性，使它们成为有用的抗焦虑和抗精神病药物。还描述了一种制备它们的方法和含有它们的药物组合物。

  公开号：

  US04728649A1

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。
• 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.
• 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
• 3-oxo-piperazin-1-yl-ergolines exhibiting antidopaminergic activity
  申请人：Farmitalia Carlo Erba

  公开号：US04728649A1

  公开（公告）日：1988-03-01

  The invention relates to ergoline derivatives having the general formula (I): ##STR1## where R=H, CH.sub.3 ; R.sub.1 =H, halogen, CH.sub.3, phenylthio, C.sub.1 -C.sub.4 alkylthio; R.sub.2 =H, CH.sub.3 O, and R.sub.3 =H or R.sub.2 +R.sub.3 =chemical bond; R.sub.4 =C.sub.1 -C.sub.4 hydrocarbon; R.sub.5, R.sub.6, R.sub.8, R.sub.9 independently=H, C.sub.1 -C.sub.4 alkyl, or R.sub.5, R.sub.8 independently=H, C.sub.1 -C.sub.4 alkyl and R.sub.6 +R.sub.9 =CH.sub.2 CH.sub.2, CH.sub.2 CH.sub.2 CH.sub.2 ; R.sub.7 =H, C.sub.1 -C.sub.4 alkyl, phenyl, NR'R"; R',R" independently=H, C.sub.1 -C.sub.4 alkyl, acyl or NR'R"=heterocyclic ring; W=0, H.sub.2 ; n=0, 1, 2, and their pharmaceutically acceptable salts, these compounds exhibiting antihypertensive activity making them useful anxiolytic and antipsychotic agents. A process for their preparation and pharmaceutical compositions containing them are also described.

  该发明涉及具有一般式（I）的麦角酸衍生物：其中R=H，CH3；R1=H，卤素，CH3，苯硫醚，C1-C4烷硫基；R2=H，CH3O，R3=H或R2+R3=化学键；R4=C1-C4碳氢化合物；R5、R6、R8、R9独立地=H，C1-C4烷基，或R5、R8独立地=H，C1-C4烷基和R6+R9=CH2CH2，CH2CH2CH2；R7=H，C1-C4烷基，苯基，NR'R"；R'，R"独立地=H，C1-C4烷基，酰基或NR'R"=杂环；W=0，H2；n=0，1，2，及其药学上可接受的盐，这些化合物具有降压活性，使它们成为有用的抗焦虑和抗精神病药物。还描述了一种制备它们的方法和含有它们的药物组合物。