N-Ethoxycarbonyl-p-toluylsulfinsaeureamid | 18513-04-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-Ethoxycarbonyl-p-toluylsulfinsaeureamid
• CAS: 18513-04-7
• 化学式: C₁₀H₁₃NO₃S
• 分子量: 227.284
• InChiKey: ZZOTVXTYJYOJDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  哌啶 、 N-Ethoxycarbonyl-p-toluylsulfinsaeureamid 在 N-氯代丁二酰亚胺 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 1-(4-methylphenylsulfonimidoyl)piperidine
  参考文献：
  名称：

  Pd催化的乙烯基溴化物和磺酰亚胺酰胺的C–N偶联：N'-乙烯基磺酰亚胺酰胺的简便合成†

  摘要：

  N'-乙烯基磺酰亚胺酰胺是通过Pd催化的N'-脱保护的磺酰亚胺酰胺的N '-（亚胺氮）与乙烯基溴之间的C-N交叉偶联而合成的。迄今为止从未报道过的产物以中等至极好的收率获得，并且在反应过程中保留了乙烯基底物的C-C双键几何形状。单晶X射线晶体学分析证实了产物结构。此外，我们证明了形成的N'-乙烯基磺酰亚胺酰胺可以与Pd–C / H 2进行氢化，以提供N'-烷基磺酰亚胺酰胺。

  DOI：

  10.1039/c5ra10939f
• 作为产物：
  描述：

  对甲苯亚磺酸甲酯 在 正丁基锂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 N-Ethoxycarbonyl-p-toluylsulfinsaeureamid
  参考文献：
  名称：

  N-Trifluoromethylthiolated Sulfonimidamides and Sulfoximines: Anti-microbial, Anti-mycobacterial, and Cytotoxic Activity

  摘要：

  Herein we demonstrate the expanded utility of a recently described N-trifluoromethylthiolation protocol to sulfonimidamide containing substances. The novel N-trifluoromethylthio sulfonimidamide derivatives thus obtained were evaluated for antibacterial activity against Mycobacterium tuberculosis (M. tb.) and Mycobacterium abscessus and Gram + Ve (Streptococcus aureus, Bacillus subtilis), and Gram - Ve (Escherichia coli, Pseudomonas aeruginosa) bacteria. Two compounds, 13 and 15 showed high antimycobacterial activity with MIC value of 4-8 mu g/mL; i.e. comparable to WHO recommended first line antibiotic for TB infection ethambutol. The same compounds were also found to be cytotoxic in HepG2 cells (compound 13 IC50 = 15 mu g/mL; compound 15 IC50 = 65 mu g/mL). A structure activity relationship, using matched pair analysis, gave the unexpected conclusion that the trifluoromethylthio moiety was responsible for the cellular and bacterial toxicity. Given the increasing use of the trifluoromethylthio group in contemporary medicinal chemistry, this observation calls for considerations before implementation of the functionality in drug design.

  DOI：

  10.1021/acsmedchemlett.9b00285