8,9-didehydro-8-methyl-2-(methylthio)ergoline | 104004-06-0

• 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: 8,9-didehydro-8-methyl-2-(methylthio)ergoline
• 英文别名: 9-Methyl-5-methylsulfanyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinoline；(6aR,10aR)-9-methyl-5-methylsulfanyl-4,6,6a,7,8,10a-hexahydroindolo[4,3-fg]quinoline
• CAS: 104004-06-0
• 化学式: C₁₆H₁₈N₂S
• 分子量: 270.398
• InChiKey: ZTYYZZHHXLIHHV-BXUZGUMPSA-N

物化性质

• 沸点：
  479.3±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-碘代丙烷 、 8,9-didehydro-8-methyl-2-(methylthio)ergoline 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以40%的产率得到8,9-Didehydro-8-methyl-6-propyl-2-methylthioergoline
  参考文献：
  名称：

  Synthesis and dopamine antagonist activity of 2-thioether derivatives of the ergoline ring system

  摘要：

  A series of 2-thioether derivatives of a number of clavine alkaloid (ergoline) ring systems have been synthesized and tested for dopamine antagonist activity. Of the compounds tested 2-(methylthio)-agroclavine (8,9-didehydro-6,8-dimethyl-2-(methylthio)ergoline) (6) was the most potent and had a profile of activity in animal models indicative of potential antipsychotic activity. The synthesis and biological activity of a number of metabolites of 6, including the 13-hydroxy derivative, are also reported.

  DOI：

  10.1021/jm00059a017
• 作为产物：
  描述：

  8,9-didehydro-6,8-dimethyl-2-(methylthio)ergoline 在 溶剂黄146 、 锌 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.0h， 生成 8,9-didehydro-8-methyl-2-(methylthio)ergoline
  参考文献：
  名称：

  Synthesis and dopamine antagonist activity of 2-thioether derivatives of the ergoline ring system

  摘要：

  A series of 2-thioether derivatives of a number of clavine alkaloid (ergoline) ring systems have been synthesized and tested for dopamine antagonist activity. Of the compounds tested 2-(methylthio)-agroclavine (8,9-didehydro-6,8-dimethyl-2-(methylthio)ergoline) (6) was the most potent and had a profile of activity in animal models indicative of potential antipsychotic activity. The synthesis and biological activity of a number of metabolites of 6, including the 13-hydroxy derivative, are also reported.

  DOI：

  10.1021/jm00059a017

文献信息

• Ergoline derivatives and their use as pharmaceuticals
  申请人：Lilly Industries Limited

  公开号：EP0180463A2

  公开（公告）日：1986-05-07

  There is described a compound of the formula in which R1 is hydrogen or C1-4 alkyl, R2 is hydrogen, C1-4 alkyl, hydroxy C1-4 alkyl, C1-4 alkoxy C14 alkyl, HSC1-4 alkyl, C1-4 alkyl-S-C1-4 alkyl, C1-4 alkylthio, optionally substituted arylthio or optionally substituted aralkylthio, and R3 is hydrogen, C1-4 alkyl, optionally substituted aryl or optionally substituted aralkyl; and salts thereof. The compounds show useful effects on the central nervous system.

  所述化合物的化学式为 其中 R1 是氢或 C1-4 烷基，R2 是氢、C1-4 烷基、羟基 C1-4 烷基、C1-4 烷氧基 C14 烷基、HSC1-4 烷基、C1-4 烷基-S-C1-4 烷基、C1-4 烷硫基、任选取代的芳硫基或任选取代的烷硫基，R3 是氢、C1-4 烷基、任选取代的芳基或任选取代的烷基；及其盐。这些化合物对中枢神经系统具有有益的作用。
• US4720498A
  申请人：——

  公开号：US4720498A

  公开（公告）日：1988-01-19
• Synthesis and dopamine antagonist activity of 2-thioether derivatives of the ergoline ring system
  作者：David E. Tupper、Ian A. Pullar、James A. Clemens、John Fairhurst、Francesca C. Risius、Graham H. Timms、Susan Wedley

  DOI：10.1021/jm00059a017

  日期：1993.4

  A series of 2-thioether derivatives of a number of clavine alkaloid (ergoline) ring systems have been synthesized and tested for dopamine antagonist activity. Of the compounds tested 2-(methylthio)-agroclavine (8,9-didehydro-6,8-dimethyl-2-(methylthio)ergoline) (6) was the most potent and had a profile of activity in animal models indicative of potential antipsychotic activity. The synthesis and biological activity of a number of metabolites of 6, including the 13-hydroxy derivative, are also reported.