13-bromo-8,9-didehydro-6,8-dimethyl-2-(methylthio)ergoline | 147238-61-7

• 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: 13-bromo-8,9-didehydro-6,8-dimethyl-2-(methylthio)ergoline
• 英文别名: (6aR,10aR)-2-bromo-7,9-dimethyl-5-methylsulfanyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinoline
• CAS: 147238-61-7
• 化学式: C₁₇H₁₉BrN₂S
• 分子量: 363.321
• InChiKey: VVZLHSZLGOZMJI-IAQYHMDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  44.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  13-bromo-8,9-didehydro-6,8-dimethyl-2-(methylthio)ergoline 在 copper(l) iodide 、 三氯化铝 、 sodium methylate 、 乙硫醇 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 8,9-didehydro-6,8-dimethyl-13-hydroxy-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
• 作为产物：
  描述：

  8,9-didehydro-6,8-dimethyl-2-(methylthio)ergoline 在 pyridinium hydrobromide perbromide 作用下， 以 甲醇 为溶剂， 以66.5%的产率得到13-bromo-8,9-didehydro-6,8-dimethyl-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

• 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.