(+/-)-(3β,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-3-<(mesyloxy)methyl>-1,6-dimethoxybenzoquinoline | 87056-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (+/-)-(3β,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-3-<(mesyloxy)methyl>-1,6-dimethoxybenzoquinoline
• 英文别名: [(3S,4aS,10aS)-1,6-dimethoxy-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-3-yl]methyl methanesulfonate
• CAS: 87056-82-4
• 化学式: C₁₇H₂₅NO₅S
• 分子量: 355.455
• InChiKey: OKUYRLKIIPNTHO-NOLJZWGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-(3β,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-3-<(mesyloxy)methyl>-1,6-dimethoxybenzoquinoline 在 三溴化硼 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (+/-)-(3β,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-6-hydroxy-3-<(methylthio)methyl>-1-propylbenzoquinoline
  参考文献：
  名称：

  Octahydrobenzo[g]quinolines: potent dopamine agonists which show the relationship between ergolines and apomorphine

  摘要：

  A synthesis of all four diastereoisomeric 3-(tert-butoxycarbonyl)-1,6-dimethoxyoctahydrobenzo[g]quinolines 13a-d is presented. The two trans isomers 13b and 13c have been converted to tricyclic analogues 20 (CV 205-502) and 26 (205-503) of the potent dopaminomimetic ergolines CQ 32-084 and pergolide, respectively. These two compounds combine the essential moiety of apomorphine with the important 8-substituents of ergolines. Preliminary pharmacological evaluation of 20 and 26 suggests that these novel dopamine agonists combine the specificity of apomorphine with the potency, long duration of action, and good oral activity of the ergolines.

  DOI：

  10.1021/jm00381a017
• 作为产物：
  描述：

  (+/-)-(3β,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxy-3-(methoxycarbonyl)benzoquinoline 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (+/-)-(3β,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-3-<(mesyloxy)methyl>-1,6-dimethoxybenzoquinoline
  参考文献：
  名称：

  Octahydrobenzo[g]quinolines: potent dopamine agonists which show the relationship between ergolines and apomorphine

  摘要：

  A synthesis of all four diastereoisomeric 3-(tert-butoxycarbonyl)-1,6-dimethoxyoctahydrobenzo[g]quinolines 13a-d is presented. The two trans isomers 13b and 13c have been converted to tricyclic analogues 20 (CV 205-502) and 26 (205-503) of the potent dopaminomimetic ergolines CQ 32-084 and pergolide, respectively. These two compounds combine the essential moiety of apomorphine with the important 8-substituents of ergolines. Preliminary pharmacological evaluation of 20 and 26 suggests that these novel dopamine agonists combine the specificity of apomorphine with the potency, long duration of action, and good oral activity of the ergolines.

  DOI：

  10.1021/jm00381a017

文献信息

• US5262422A
  申请人：——

  公开号：US5262422A

  公开（公告）日：1993-11-16
• Octahydrobenzo[g]quinolines: potent dopamine agonists which show the relationship between ergolines and apomorphine
  作者：Rene Nordmann、Trevor J. Petcher

  DOI：10.1021/jm00381a017

  日期：1985.3

  A synthesis of all four diastereoisomeric 3-(tert-butoxycarbonyl)-1,6-dimethoxyoctahydrobenzo[g]quinolines 13a-d is presented. The two trans isomers 13b and 13c have been converted to tricyclic analogues 20 (CV 205-502) and 26 (205-503) of the potent dopaminomimetic ergolines CQ 32-084 and pergolide, respectively. These two compounds combine the essential moiety of apomorphine with the important 8-substituents of ergolines. Preliminary pharmacological evaluation of 20 and 26 suggests that these novel dopamine agonists combine the specificity of apomorphine with the potency, long duration of action, and good oral activity of the ergolines.