6,7-dimethoxy-2-(methylthio)tetralin | 89017-47-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6,7-dimethoxy-2-(methylthio)tetralin
• 英文别名: 6,7-Dimethoxy-2-(methylsulfanyl)-1,2,3,4-tetrahydronaphthalene；6,7-dimethoxy-2-methylsulfanyl-1,2,3,4-tetrahydronaphthalene
• CAS: 89017-47-0
• 化学式: C₁₃H₁₈O₂S
• 分子量: 238.351
• InChiKey: AYCGXYLJDMUGJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 6,7-dimethoxy-2-(methylthio)tetralin 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到(6,7-dihydroxy-2-tetralinyl)dimethylsulfonium bromide
  参考文献：
  名称：

  Dopaminergic agonists: comparative actions of amine and sulfonium analogs of dopamine

  摘要：

  We have investigated the possibility that structural modifications of the sulfonium analogue of dopamine (4) would produce the same pattern of biological activity as structural modifications of dopamine. A series of methyl- tetralinyl -, and naphthalenylsulfonium analogues 5-7 were prepared and tested for their ability to inhibit the potassium-evoked release of [3H]acetylcholine from striatal slices. All compounds were tested under normal conditions and after depletion of dopamine stores with reserpine and alpha-methyl-p-tyrosine. The amine and sulfonium analogues 2-6 all showed direct agonist activity. The sulfonium analogue 7 produced, predominantly, indirect activity. In contrast to the amine analogues, chemical modifications of the sulfonium compounds produced little change in their dopamine agonist activity.

  DOI：

  10.1021/jm00371a021
• 作为产物：
  描述：

  1,2-二氢-6,7-二甲氧基萘 在 三乙基硅烷 、 碳酸氢钠 、 三氟乙酸 作用下， 以 苯 为溶剂， 反应 7.17h， 生成 6,7-dimethoxy-2-(methylthio)tetralin
  参考文献：
  名称：

  Dopaminergic agonists: comparative actions of amine and sulfonium analogs of dopamine

  摘要：

  We have investigated the possibility that structural modifications of the sulfonium analogue of dopamine (4) would produce the same pattern of biological activity as structural modifications of dopamine. A series of methyl- tetralinyl -, and naphthalenylsulfonium analogues 5-7 were prepared and tested for their ability to inhibit the potassium-evoked release of [3H]acetylcholine from striatal slices. All compounds were tested under normal conditions and after depletion of dopamine stores with reserpine and alpha-methyl-p-tyrosine. The amine and sulfonium analogues 2-6 all showed direct agonist activity. The sulfonium analogue 7 produced, predominantly, indirect activity. In contrast to the amine analogues, chemical modifications of the sulfonium compounds produced little change in their dopamine agonist activity.

  DOI：

  10.1021/jm00371a021

文献信息

• Dopaminergic agonists: comparative actions of amine and sulfonium analogs of dopamine
  作者：Akihiko Hamada、Yu An Chang、Norman Uretsky、Duane D. Miller

  DOI：10.1021/jm00371a021

  日期：1984.5

  We have investigated the possibility that structural modifications of the sulfonium analogue of dopamine (4) would produce the same pattern of biological activity as structural modifications of dopamine. A series of methyl- tetralinyl -, and naphthalenylsulfonium analogues 5-7 were prepared and tested for their ability to inhibit the potassium-evoked release of [3H]acetylcholine from striatal slices. All compounds were tested under normal conditions and after depletion of dopamine stores with reserpine and alpha-methyl-p-tyrosine. The amine and sulfonium analogues 2-6 all showed direct agonist activity. The sulfonium analogue 7 produced, predominantly, indirect activity. In contrast to the amine analogues, chemical modifications of the sulfonium compounds produced little change in their dopamine agonist activity.