8β-<(3,5-dioxo-4-aminopiperazin-1-yl)methyl>-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-dioxo-4-aminopiperazin-1-yl)methyl>-6-methylergoline
• 英文别名: 6-methyl-8β-(3,5-dioxo-4-amino-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]-1-aminopiperazine-2,6-dione
• 化学式: C₂₀H₂₅N₅O₂
• 分子量: 367.451
• InChiKey: HMGQXIJWKWNMMK-SRCQZFHVSA-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：
  0.5
• 拓扑面积：
  85.7
• 氢给体数：
  2
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	8β-<(3,5-dioxo-4-aminopiperazin-1-yl)methyl>-9,10-didehydro-6-methylergoline	107052-58-4	C20H23N5O2	365.435
  ——	2-[[(6aR,9S)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]methyl-(2-hydrazinyl-2-oxoethyl)amino]acetohydrazide	1025807-21-9	C20H27N7O2	397.48
  ——	N-<(9,10-didehydro-6-methylergolin-8β-yl)methyl>-iminodiacetic acid diethyl ester	229156-14-3	C24H31N3O4	425.528

反应信息

• 作为产物：
  描述：

  N-<(9,10-didehydro-6-methylergolin-8β-yl)methyl>-iminodiacetic acid diethyl ester 在 palladium on activated charcoal 氢气 、 一水合肼 、 苯酚 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 25.0~160.0 ℃ 、303.98 kPa 条件下， 反应 2.0h， 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

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：EP0197241A1

  公开（公告）日：1986-10-15

  Compounds I (R = H, CH3; R, = H, halogen, CH3, phenylthio, C, - C4 alkylthio; R2 = H, CH30 and R3 = H or R2 + R3 = chemical bond; R4 = C, - C4 hydrocarbon; R5, Rs, R8, R9 independently = H, C, - C4 alkyl or R5, R8 independently = H, C, - C4 alkyl and R6 + R9 = CH2CH7,CH2CH2CH2; R7 = H, C1 - C4 alkyl, phenyl, NR'R"; R', R" independently = H, C, - C4 alkyl, acyl or NR' R" = heterocyclic ring; W = 0, H2; n = O, 1, 2) and their pharmaceutically acceptable salts have antihypertensive activity and are useful anxiolytic and antipsychotic agents. A process for their preparation and pharmaceutical composition containing them are also described.

  化合物 I（R = H、CH3；R, = H、卤素、CH3、苯硫基、C、-C4 烷硫基；R2 = H、CH30 和 R3 = H 或 R2 + R3 = 化学键；R4 = C、-C4 烃；R5、Rs、R8、R9 独立地 = H、C、-C4 烷基或 R5、R8 独立地 = H、C、-C4 烷基和 R6 + R9 = CH2CH7、CH2CH2CH2；R7 = H、C1 - C4 烷基、苯基、NR'R"；R'、R" 独立地 = H、C、- C4 烷基、酰基或 NR' R" = 杂环；W = 0、H2；n = O、1、2）及其药学上可接受的盐具有降压活性，是有用的抗焦虑和抗精神病药物。本文还描述了它们的制备过程和含有它们的药物组合物。
• 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.