6-Methyl-8-β-formyl-ergoline | 22595-09-1

• 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: 6-Methyl-8-β-formyl-ergoline
• 英文别名: (6aR,9R,10aR)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carbaldehyde
• CAS: 22595-09-1
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: ANIZVIVSQJFTBV-WDBKCZKBSA-N

物化性质

• 沸点：
  170-171 °C
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Methyl-8-β-formyl-ergoline 在 sodium hydroxide 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.75h， 生成 (E)-3-(6-Methyl-ergolin-8β-yl)acrylic acid
  参考文献：
  名称：

  Synthesis and in vitro and in vivo evaluation of dopaminergic ergoline derivatives

  摘要：

  A series of ergoline-amides was synthesised in the discovery of new dopaminomimetic agents. Several compounds exhibited in vivo high prolactin lowering activity (indirectly measured by the nidation test) in rats. For the most active, the potential anti-Parkinson activity was evaluated by observation of the contralateral turning behaviour in 6-OH-DA lesioned rats. The acute toxicity by oral route in mice was also studied. (C) 1998 Elsevier Science S.A.

  DOI：

  10.1016/s0014-827x(97)00009-8
• 作为产物：
  描述：

  6-甲基麦角灵-8β-甲醇 在 TEA*SO₃ 、 TEA 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 以82%的产率得到6-Methyl-8-β-formyl-ergoline
  参考文献：
  名称：

  Synthesis and in vitro and in vivo evaluation of dopaminergic ergoline derivatives

  摘要：

  A series of ergoline-amides was synthesised in the discovery of new dopaminomimetic agents. Several compounds exhibited in vivo high prolactin lowering activity (indirectly measured by the nidation test) in rats. For the most active, the potential anti-Parkinson activity was evaluated by observation of the contralateral turning behaviour in 6-OH-DA lesioned rats. The acute toxicity by oral route in mice was also studied. (C) 1998 Elsevier Science S.A.

  DOI：

  10.1016/s0014-827x(97)00009-8

文献信息

• Ergoline derivatives, process for preparing them, pharmaceutical composition and use
  申请人：FARMITALIA CARLO ERBA S.r.l.

  公开号：EP0206206A1

  公开（公告）日：1986-12-30

  Ergoline derivatives of the formula I wherein R1=H, CH3; R2=H, halogen, CH3, CN, C1-C4 alkylthio or phenylthio; R3=C1-C4 hydrocarbon; R4=H, OCH3; R5=H and R6=-CH=CH-CONHR7 or R5 + R6= =CH-CONHR7; R7= 2-thiazolyl, 3-pyridazinyl, 1,3,4-thiadiazol-2-yl or 4-pyrimidinyl group optionally substituted, and pharmaceutically acceptable salts thereof, display activity on the Central Nervous System and are useful as antiprolactinic agents. Their preparation, pharmaceutical compositions containing them, and their use in the preparation of a medicament for the treatment of Parkinson's disease are also described.

  式 I 的麦角啉衍生物 其中 R1=H, CH3; R2=H, 卤素, CH3, CN, C1-C4 烷硫基或苯硫基; R3=C1-C4 碳氢化合物; R4=H, OCH3; R5=H 和 R6=-CH=CH-CONHR7 或 R5 + R6= =CH-CONHR7；R7= 2-噻唑基、3-哒嗪基、1,3,4-噻二唑-2-基或任选取代的 4-嘧啶基，以及它们的药学上可接受的盐，对中枢神经系统具有活性，可用作抗催乳素药。此外，还介绍了它们的制备方法、含有它们的药物组合物以及它们在制备治疗帕金森病的药物中的用途。
• Studies on oxidation of ergot alkaloids: oxidation and desaturation of dihydrolysergol—stereochemical requirements
  作者：Radek Gažák、Vladimír Křen、Petr Sedmera、Daniele Passarella、Michaela Novotná、Bruno Danieli

  DOI：10.1016/j.tet.2007.07.099

  日期：2007.10

  A new method for the oxidation of ergoline alcohols to aldehydes was found (TFFA-DMSO, -78 degrees C, then DIPEA). Structural features of ergolines required for successful C7-C8 double bond introduction via Polonovski-Potier reaction of respective 6-N-oxides were defined and experimentally confirmed: (i) the presence of electron-withdrawing group at C-8; (ii) trans-diaxial orientation of N6-O and C7-H bonds ( both requirements are fulfilled for dihydrolyserg-17-al and its 2,4-dinitrophenyl hydrazone prepared in this work). (c) 2007 Published by Elsevier Ltd.
• US4746666A
  申请人：——

  公开号：US4746666A

  公开（公告）日：1988-05-24
• Synthesis and in vitro and in vivo evaluation of dopaminergic ergoline derivatives
  作者：Sergio Mantegani、Enzo Brambilla、Carla Caccia、Enrico Di Salle、Maria Antonietta Cervini、Robert A. McArthur、Gabriella Traquandi、Mario Varasi

  DOI：10.1016/s0014-827x(97)00009-8

  日期：1998.1

  A series of ergoline-amides was synthesised in the discovery of new dopaminomimetic agents. Several compounds exhibited in vivo high prolactin lowering activity (indirectly measured by the nidation test) in rats. For the most active, the potential anti-Parkinson activity was evaluated by observation of the contralateral turning behaviour in 6-OH-DA lesioned rats. The acute toxicity by oral route in mice was also studied. (C) 1998 Elsevier Science S.A.