2-chloro-10-<3-(methylthio)propyl>phenothiazine | 109011-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-chloro-10-<3-(methylthio)propyl>phenothiazine
• 英文别名: 2-chloro-10-[3-(methylthio)propyl]phenothiazine；2-chloro-10-(3-methylsulfanylpropyl)phenothiazine
• CAS: 109011-74-7
• 化学式: C₁₆H₁₆ClNS₂
• 分子量: 321.895
• InChiKey: KVTJNJQZFIRIDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-chloro-10-<3-(methylthio)propyl>phenothiazine 、 碘甲烷 以58%的产率得到
  参考文献：
  名称：

  HARROLD, MARC W.;CHANG, YU-AN;WALLACE, RAYE ANN;FAROOQUI, TAHIRA;WALLACE,+, J. MED. CHEM., 30,(1987) N 9, 1631-1635

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯吩噻嗪 在 氢氧化钾 、 sodium hydride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 29.0h， 生成 2-chloro-10-<3-(methylthio)propyl>phenothiazine
  参考文献：
  名称：

  Charged analogs of chlorpromazine as dopamine antagonists

  摘要：

  Chlorpromazine (1, CPZ) is a potent dopamine antagonist that has been used widely as an antipsychotic agent. Since dopaminergic antagonists, like dopaminergic agonists, exist in solution as the charged and uncharged molecular species, it is not clear which form of the amine is most important for interaction with the dopamine receptor. Previous work from our laboratory has indicated that a variety of permanently charged species could replace the amine/ammonium moiety of dopamine and retain dopamine agonist activity. This paper describes the synthesis and dopamine antagonist activity of both the trimethylammonium iodide and the dimethylsulfonium iodide analogues of chlorpromazine. The permanently uncharged methyl sulfide analogue was also synthesized; however, due to its lack of aqueous solubility, its pharmacological activity could not be evaluated. Binding of both the dimethylsulfonium iodide and the trimethylammonium iodide analogues to D-2 dopamine receptors of rat striatal tissue was observed. The observed relative order of binding was CPZ greater than CPZ sulfonium analogue greater than CPZ ammonium analogue. These compounds had a similar order of activity in antagonizing the apomorphine-induced inhibition of potassium-induced release of [3H]acetylcholine from mouse striatal slices.

  DOI：

  10.1021/jm00392a019