N,N,N-triethyl-2-(4-(3-thioxo-3H-1,2-dithiol-5-yl)phenoxy)ethanaminium bromide | 1234493-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N,N,N-triethyl-2-(4-(3-thioxo-3H-1,2-dithiol-5-yl)phenoxy)ethanaminium bromide
• 英文别名: Triethyl-[2-[4-(5-sulfanylidenedithiol-3-yl)phenoxy]ethyl]azanium;bromide
• CAS: 1234493-54-9
• 化学式: Br*C₁₇H₂₄NOS₃
• 分子量: 434.486
• InChiKey: ATNISRWAQOQXOX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  91.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-(4-(2-bromoethoxy)phenyl)-3H-1,2-dithiole-3-thione 、 三乙胺 以70.1%的产率得到N,N,N-triethyl-2-(4-(3-thioxo-3H-1,2-dithiol-5-yl)phenoxy)ethanaminium bromide
  参考文献：
  名称：

  Design, synthesis, and pharmacological evaluation of the aqueous prodrugs of desmethyl anethole trithione with hepatoprotective activity

  摘要：

  A metabolite-based prodrug strategy to increase the solubility of anethole trithione was reported to facilitate the clinical application of this hepatoprotective agent. Water-soluble analogs of anethole trithione were synthesized via substituting the methyl group of anethole trithione with the simple hydrophilic alkylamino group, and subjected to physiochemical, pharmacological and metabolic studies. The prodrugs displayed increased solubility as well as other physiochemical properties favorable for parenteral use. Among the analogs synthesized, the compound 5a exhibited best hepatoprotective activity at the dose of 2.0 mg/kg in mice equal to that of anethole trithione. The in vivo metabolic investigation demonstrated that the straight-side chain prodrug 5a could convert to desmethyl anethole trithione in vivo, while the ring-side chain prodrug 5d could not. The hepatoprotective activity of the prodrugs might result from the active metabolite desmethyl anethole trithione. (c) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.029

文献信息

• Design, synthesis, and pharmacological evaluation of the aqueous prodrugs of desmethyl anethole trithione with hepatoprotective activity
  作者：Pei Chen、Yu Luo、Li Hai、Shan Qian、Yong Wu

  DOI：10.1016/j.ejmech.2010.03.029

  日期：2010.7

  A metabolite-based prodrug strategy to increase the solubility of anethole trithione was reported to facilitate the clinical application of this hepatoprotective agent. Water-soluble analogs of anethole trithione were synthesized via substituting the methyl group of anethole trithione with the simple hydrophilic alkylamino group, and subjected to physiochemical, pharmacological and metabolic studies. The prodrugs displayed increased solubility as well as other physiochemical properties favorable for parenteral use. Among the analogs synthesized, the compound 5a exhibited best hepatoprotective activity at the dose of 2.0 mg/kg in mice equal to that of anethole trithione. The in vivo metabolic investigation demonstrated that the straight-side chain prodrug 5a could convert to desmethyl anethole trithione in vivo, while the ring-side chain prodrug 5d could not. The hepatoprotective activity of the prodrugs might result from the active metabolite desmethyl anethole trithione. (c) 2010 Elsevier Masson SAS. All rights reserved.