paspalic acid | 5516-88-1

• 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: paspalic acid
• 英文别名: 6-methyl-8,9-didehydro-ergoline-8-carboxylic acid；6-Methyl-Δ^8,9-ergolen-carbonsaeure-(8)；6-Methyl-8(9)-ergolen-8-carbonsaeure；Paspalate；(6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydroindolo[4,3-fg]quinolin-7-ium-9-carboxylate
• CAS: 5516-88-1
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: RJNCJTROKRDRBW-TZMCWYRMSA-N

物化性质

• 熔点：
  245-247 °C (decomp)
• 沸点：
  536.1±50.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  56.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  paspalic acid 在 palladium on activated charcoal 氢气 作用下， 生成 9,10-二氢麦角酸
  参考文献：
  名称：

  Ergoline derivatives as highly potent and selective antagonists at the somatostatin sst1 receptor

  摘要：

  Non-peptidic compounds containing the octahydro-indolo[4,3-fg]quinoline (ergoline) structural element have been optimized into derivatives with high affinity (pK(d) r sst(1) > 9) and selectivity (> 1000-fold for h sst(1) over h sst(2)-h sst(5)) for the somatostatin sst(1) receptor. In functional assays, these ergolines act as antagonists at human recombinant sst(1) receptors. Pharmacokinetic studies in rodents reveal good oral bioavailability and brain penetration for some of these compounds. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.030
• 作为试剂：
  描述：

  sodium hydroxide 、 paspalic acid 、 硫酸 在 氮气 、 (+)-麦角酸硫酸盐 、 甲醇 、 氨 、 水 、 麦角酸 、 paspalic acid 、 D-异麦角酸 作用下， 以 水 为溶剂， 5.0~60.0 ℃ 、399.97 kPa 条件下， 反应 54.0h， 以lysergic acid (90.8 g) was obtained (titration assay 98.7%, content of paspalic acid 0.6%, content of isolysergic acid 0.9%)的产率得到麦角酸
  参考文献：
  名称：

  Process for the manufacture of lysergic acid

  摘要：

  利酸通过在巴斯帕利酸和浓缩水合金属氢氧化物溶液形成的相分离混合物中异构化巴斯帕利酸而高产高质地形成。

  公开号：

  US20070135638A1

文献信息

• [EN] PROCESS FOR THE MANUFACTURE OF LYSERGIC ACID<br/>[FR] PROCESSUS DE FABRICATION D'ACIDE LYSERGIQUE
  申请人：IVAX CORP

  公开号：WO2005082902A1

  公开（公告）日：2005-09-09

  Lysergic acid is formed in high yields and high quality by isomerizing paspalic acid in a phase separated mixture formed by paspalic acid and a concentrated aqueous metal hydroxide solution.

  利用由帕斯帕酸和浓缩水性金属氢氧化物溶液组成的相分离混合物，通过异构化帕斯帕酸高产高质地形成溴酸。
• Process of preparing lysergic acid
  申请人：Aventis Pharma S.A.

  公开号：US06242603B1

  公开（公告）日：2001-06-05

  The present invention relates to a novel process for preparing lysergic acid by isomerizing paspalic acid, using a tetraalkylammonium hydroxide.

  本发明涉及一种使用四烷基氢氧化铵异构化帕斯帕利酸制备麦角酸的新工艺。
• PREPARATION OF MICROBIOLOGICALLY PRODUCED ERGOT ALKALOIDS
  申请人：Bertel Stephan

  公开号：US20110137035A1

  公开（公告）日：2011-06-09

  The present invention relates to a method for preparing microbiologically produced ergot alkaloids of the following formula (I), comprising the step of: a) extracting the fermentation product occurring during the biological production, said product containing at least one ergot alkaloid of formula (I), at a pH of 8-14 using an extractant with a solubility in water of 0.2 g/100 g of water to 25 g/100 g water at 20° C., wherein the amount of extractant is sufficient to form a 2-phase system together with the fermentation product.
• Ergoline derivatives as highly potent and selective antagonists at the somatostatin sst1 receptor
  作者：Thomas Troxler、Albert Enz、Daniel Hoyer、Daniel Langenegger、Peter Neumann、Paul Pfäffli、Philippe Schoeffter、Konstanze Hurth

  DOI：10.1016/j.bmcl.2007.12.030

  日期：2008.2

  Non-peptidic compounds containing the octahydro-indolo[4,3-fg]quinoline (ergoline) structural element have been optimized into derivatives with high affinity (pK(d) r sst(1) > 9) and selectivity (> 1000-fold for h sst(1) over h sst(2)-h sst(5)) for the somatostatin sst(1) receptor. In functional assays, these ergolines act as antagonists at human recombinant sst(1) receptors. Pharmacokinetic studies in rodents reveal good oral bioavailability and brain penetration for some of these compounds. (C) 2007 Elsevier Ltd. All rights reserved.
• Process for the manufacture of lysergic acid
  申请人：Cvak Ladislav

  公开号：US20070135638A1

  公开（公告）日：2007-06-14

  Lysergic acid is formed in high yields and high quality by isomerizing paspalic acid in a phase separated mixture formed by paspalic acid and a concentrated aqueous metal hydroxide solution.

  利酸通过在巴斯帕利酸和浓缩水合金属氢氧化物溶液形成的相分离混合物中异构化巴斯帕利酸而高产高质地形成。