<2-(3,4-dhydroxyphenyl)ethyl>dimethylsulfonium iodide | 77263-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: <2-(3,4-dhydroxyphenyl)ethyl>dimethylsulfonium iodide
• 英文别名: [2-(3,4-dhydroxyphenyl)ethyl]dimethylsulfonium iodide；2-(3,4-Dihydroxyphenyl)ethyl-dimethylsulfanium;iodide
• CAS: 77263-40-2
• 化学式: C₁₀H₁₅O₂S*I
• 分子量: 326.198
• InChiKey: DQILVOWYCKLIMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.48
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3',4'-(methylenedioxy)-2-(methylsulfinyl)acetophenone 在 三乙基硅烷 、 三甲基氯硅烷 、 三氯化硼 、 三氟乙酸 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 34.0h， 生成 <2-(3,4-dhydroxyphenyl)ethyl>dimethylsulfonium iodide
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of sulfonium analogs of dopamine: nonclassical dopamine agonists

  摘要：

  In order to test whether the nitrogen/ammonium moiety in the dopamine molecule is required for dopaminergic activity, we have synthesized two sulfonium analogues of dopamine and tested them for biological activity in an in vivo and in an in vitro system. These analogues have provided a means of investigating (1) the ability of the sulfonium function to serve as a bioisostere for the dopamine amino group and (2) whether charged molecules have the ability to bind to dopamine receptors. Both sulfonium analogues, 1 and 2, as well as dopamine, when injected directly into the striatum of rats, previously lesioned unilaterally with 6-hydroxydopamine (6-OHDA), produced circling behavior. The potency of the sulfonium analogues was approximately one-tenth that of dopamine. The effects of all three compounds on circling were inhibited by the dopamine antagonist haloperidol. In addition, both sulfonium analogues inhibited the high affinity binding of radiolabeled dopamine to a crude membrane fraction prepared from the striatum. This study suggests that the nitrogen atom found in th dopamine molecule is not essential for dopaminergic activity, since the nitrogen can be replaced by a sulfonium functional group for this activity.

  DOI：

  10.1021/jm00138a008

文献信息

• Synthesis and pharmacological evaluation of sulfonium analogs of dopamine: nonclassical dopamine agonists
  作者：Karen Anderson、Alice Kuruvilla、Norman Uretsky、Duane D. Miller

  DOI：10.1021/jm00138a008

  日期：1981.6

  In order to test whether the nitrogen/ammonium moiety in the dopamine molecule is required for dopaminergic activity, we have synthesized two sulfonium analogues of dopamine and tested them for biological activity in an in vivo and in an in vitro system. These analogues have provided a means of investigating (1) the ability of the sulfonium function to serve as a bioisostere for the dopamine amino group and (2) whether charged molecules have the ability to bind to dopamine receptors. Both sulfonium analogues, 1 and 2, as well as dopamine, when injected directly into the striatum of rats, previously lesioned unilaterally with 6-hydroxydopamine (6-OHDA), produced circling behavior. The potency of the sulfonium analogues was approximately one-tenth that of dopamine. The effects of all three compounds on circling were inhibited by the dopamine antagonist haloperidol. In addition, both sulfonium analogues inhibited the high affinity binding of radiolabeled dopamine to a crude membrane fraction prepared from the striatum. This study suggests that the nitrogen atom found in th dopamine molecule is not essential for dopaminergic activity, since the nitrogen can be replaced by a sulfonium functional group for this activity.