triethylamine thiomorpholine-4-carbodithioate | 1381994-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻嗪类
• 英文名称: triethylamine thiomorpholine-4-carbodithioate
• CAS: 1381994-39-3
• 化学式: C₅H₉NS₃*C₆H₁₅N
• 分子量: 280.523
• InChiKey: NQSSGSMENBNOIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  6.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  triethylamine thiomorpholine-4-carbodithioate 、 2,4-二硝基氟苯 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2,4-dinitrophenyl thiomorpholine-4-carbodithioate
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of 2,4-Dinitroaryldithiocarbamate Derivatives as Novel Monoacylglycerol Lipase Inhibitors

  摘要：

  Monoacylglycerol lipase (MAGL) is responsible for signal termination of 2-arachidonoylglycerol (2-AG), an endocannabinoid neurotransmitter endowed with several physiological effects. Previously, we showed that the arylthioamide scaffold represents a privileged template for designing MAGL inhibitors. A series of 37 compounds resulting from pharmacomodulations around the arylthioamide template were synthesized and tested to evaluate their inhibitory potential on MAGL activity as well as their selectivity over fatty acid amide hydrolase (FAAH), another endocannabinoid-hydrolyzing enzyme. We have identified 2,4-dinitroaryldithiocarbamate derivatives as a novel class of MAGL inhibitors. Among the synthesized compounds, we identified [2,4-dinitrophenyl-4-(4-tert-butylbenzyl)piperazine-1-carbodithioate] (CK37), as the most potent MAGL inhibitor within this series (IC50= 154 nM). We have also identified [2,4-dinitrophenyl-4-benzhydrylpiperazine-1-carbodithioate] (CK16) as a selective MAGL inhibitor. These compounds are irreversible MAGL inhibitors that probably act by interacting with Cys208 or Cys242 and Ser122 residues of the enzyme. Moreover, CK37 is able to raise 2-arachidonoylglycerol (2-AG) levels in intact cells.

  DOI：

  10.1021/jm3006004
• 作为产物：
  描述：

  硫代吗啉 、 二硫化碳 、 三乙胺 以 乙腈 为溶剂， 反应 0.42h， 生成 triethylamine thiomorpholine-4-carbodithioate
  参考文献：
  名称：

  使用原位生成的二硫代氨基甲酸酯来合成芳基胺的三取代硫脲的非异硫氰酸酯途径†

  摘要：

  首次提出了一种使用原位生成的仲胺的二硫代氨基甲酸酯合成新颖，用户友好且方便的芳基胺的三取代硫脲的方法。该策略为获得含有伯芳基胺的硫脲提供了极好的机会。获得异硫脲的非异硫氰酸酯途径是该策略的优势，这可能为合成多种硫脲的生物活性衍生物提供了有用的途径。

  DOI：

  10.1039/c2ra23257j