4-[S-4-nitrophenyl-N-(phenylvinyl)sulfonimidoyl]morpholine | 18513-10-5

• 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: 4-[S-4-nitrophenyl-N-(phenylvinyl)sulfonimidoyl]morpholine
• 英文别名: 4-(4-nitro-benzenesulfonimidoyl)-morpholine
• CAS: 18513-10-5
• 化学式: C₁₀H₁₃N₃O₄S
• 分子量: 271.297
• InChiKey: QYVNDPXEPVVBFX-UHFFFAOYSA-N

物化性质

• 沸点：
  433.5±55.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  96.53
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-[S-4-nitrophenyl-N-(phenylvinyl)sulfonimidoyl]morpholine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 C₁₀H₁₂BrN₃O₄S
  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
• 作为产物：
  描述：

  4-硝基苯磺酰胺 在 甲酸 、 三乙胺 、 三苯基二氯化膦 作用下， 以 氯仿 、 水 、 甲苯 、 乙腈 为溶剂， 反应 48.0h， 生成 4-[S-4-nitrophenyl-N-(phenylvinyl)sulfonimidoyl]morpholine
  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

文献信息

• Pd-catalyzed C–N coupling of vinylbromides and sulfonimidamides: a facile synthesis of N′-vinylsulfonimidamides
  作者：Ganesh C. Nandi、Sudhakar R. Kota、Prasad B. Wakchaure、Praveen K. Chinthakindi、Thavendran Govender、Hendrick G. Kruger、Tricia Naicker、Per I. Arvidsson

  DOI：10.1039/c5ra10939f

  日期：——

  through a Pd-catalyzed C–N cross coupling between the N′-(imine nitrogen) of N′-deprotected sulfonimidamides and vinyl bromides. The hitherto unreported products were obtained in moderate to excellent yield, and the C–C double bond geometry of the vinylic substrates were retained during the course of reaction. Single crystal X-ray crystallographic analysis confirmed the product structure. Furthermore, we

  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。
• Cu(OAc)₂-Catalysed Oxidative Dual C-H/N-H Activation of Terminal Alkynes and<i>N</i>-Deprotected Sulfonimidamides: An Easy Access to<i>N</i>-Alkynylated Sulfonimidamides
  作者：Ganesh Chandra Nandi、Sudhakar Rao Kota、Tricia Naicker、Thavendran Govender、Hendrick G. Kruger、Per I. Arvidsson

  DOI：10.1002/ejoc.201500239

  日期：2015.5

  We report a mild and efficient Cu(OAc)2-catalysed protocol for the oxidative C–N cross-coupling of terminal alkynes and N-deprotected sulfonimidamides. The reaction leads to hitherto unknown N-alkynylated sulfonimidamides. Furthermore, we found that the synthesised N-alkynylated sulfonimidamides could undergo silica-gel-mediated hydrolysis to give the corresponding N-acyl-sulfonimidamides, as well

  我们报告了一种温和有效的 Cu(OAc)2 催化方案，用于末端炔烃和 N-脱保护的磺酰亚胺酰胺的氧化 C-N 交叉偶联。该反应导致迄今为止未知的 N-炔基化磺酰亚胺酰胺。此外，我们发现合成的 N-炔基化磺酰亚胺酰胺可以通过硅胶介导的水解得到相应的 N-酰基磺酰亚胺，以及硼烷-二甲硫醚介导的还原反应得到相应的 N-烷基化磺酰亚胺。