(5R,8R)-6-methyl-8β-hydroxymethyl-9α-hydroxyergoline | 16727-34-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: (5R,8R)-6-methyl-8β-hydroxymethyl-9α-hydroxyergoline
• 英文别名: (6aR,9R,10S,10aR)-9-(hydroxymethyl)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-10-ol
• CAS: 16727-34-7
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: BVPBVIGKHNFPDB-YEHMFOAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,8R)-6-methyl-8β-hydroxymethyl-9α-hydroxyergoline 在 sodium hydroxide 、 吡啶盐酸盐 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氯氧磷 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (R)-9-Methyl-7-methylene-2,7,8,9,9a,10-hexahydro-pyrrolo[3',2':5,6]cyclohepta[1,2,3-cd]indole
  参考文献：
  名称：

  5(10→9)Abeo-ergoline derivatives: Synthesis, 5-HT1A-receptor affinity and selectivity

  摘要：

  The synthesis and the structure-affinity relationship (S.A.F.I.R.) study for the 5-HT1A receptor sites of a novel series of 5(10-->9)abeo-ergoline derivatives are presented. Most derivatives showed moderate to high affinity and selectivity for 5-HT1A receptor sites. The structure-affinity relationship pointed out the role of the substituent at position 8, and the outstanding importance of the reduction of the indole 2,3-double bond for achieving the highest 5-HT1A affinity and selectivity within the compounds presented. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80062-7
• 作为产物：
  描述：

  D-麦角酸甲酯 生成 (5R,8R)-6-methyl-8β-hydroxymethyl-9α-hydroxyergoline
  参考文献：
  名称：

  5(10→9)Abeo-ergoline derivatives: Synthesis, 5-HT1A-receptor affinity and selectivity

  摘要：

  The synthesis and the structure-affinity relationship (S.A.F.I.R.) study for the 5-HT1A receptor sites of a novel series of 5(10-->9)abeo-ergoline derivatives are presented. Most derivatives showed moderate to high affinity and selectivity for 5-HT1A receptor sites. The structure-affinity relationship pointed out the role of the substituent at position 8, and the outstanding importance of the reduction of the indole 2,3-double bond for achieving the highest 5-HT1A affinity and selectivity within the compounds presented. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80062-7

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.
• Bernardi; Bosisio; Mantegani, Arzneimittel-Forschung/Drug Research, 1983, vol. 33, # 8, p. 1094 - 1098
  作者：Bernardi、Bosisio、Mantegani、Sapini、Temperilli、Salvati、di Salle、Arcari、Bianchi

  DOI：——

  日期：——
• Synthesis of 5(10Æ9)abeo-Ergolines
  作者：Sergio Mantegani、Emanuele Arlandini、Daniela Borghi、Enzo Brambilla、Mario Varasi

  DOI：10.3987/com-97-7788

  日期：——

  Reaction of the (5 R, 8 R)-ergoline derivative (6) with the couple CCl4/(Ph)(3)P unexpectedly resulted in the formation of the novel (5 S, 8 R)-5 (10-->9)abeo-ergoline derivative. A mechanism of this transposition process is proposed.
• 5(10→9)Abeo-ergoline derivatives: Synthesis, 5-HT1A-receptor affinity and selectivity
  作者：Sergio Mantegani、Luca Baumer、Enzo Brambilla、Carla Caccia、Maria Cioia Fornaretto、Robert Albert McArthur、Mario Varasi

  DOI：10.1016/s0223-5234(98)80062-7

  日期：1998.4

  The synthesis and the structure-affinity relationship (S.A.F.I.R.) study for the 5-HT1A receptor sites of a novel series of 5(10-->9)abeo-ergoline derivatives are presented. Most derivatives showed moderate to high affinity and selectivity for 5-HT1A receptor sites. The structure-affinity relationship pointed out the role of the substituent at position 8, and the outstanding importance of the reduction of the indole 2,3-double bond for achieving the highest 5-HT1A affinity and selectivity within the compounds presented. (C) Elsevier, Paris.