5-chloro-N-(2-(4-((4-chloro-3-(trifluoromethyl)phenyl)sulfonamido)phenyl)benzo[d]oxazol-5-yl)thiophene-2-sulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-chloro-N-(2-(4-((4-chloro-3-(trifluoromethyl)phenyl)sulfonamido)phenyl)benzo[d]oxazol-5-yl)thiophene-2-sulfonamide
• 英文别名: 5-chloro-N-[2-[4-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]phenyl]-1,3-benzoxazol-5-yl]thiophene-2-sulfonamide
• 化学式: C₂₄H₁₄Cl₂F₃N₃O₅S₃
• 分子量: 648.491
• InChiKey: BCFLPZAGISXMLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  163
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2-硝基-4-氨基苯酚 在 吡啶 、 盐酸 、 tin 、 碳酸氢钠 、 溶剂黄146 、 sodium sulfate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 78.0h， 生成 5-chloro-N-(2-(4-((4-chloro-3-(trifluoromethyl)phenyl)sulfonamido)phenyl)benzo[d]oxazol-5-yl)thiophene-2-sulfonamide
  参考文献：
  名称：

  Sulfonamido-2-arylbenzoxazole GroEL/ES Inhibitors as Potent Antibacterials against Methicillin-Resistant Staphylococcus aureus (MRSA)

  摘要：

  Extending from a study we recently published examining the antitrypanosomal effects of a series of GroEL/ES inhibitors based on a pseudosymmetrical bis-sulfonamido-2-phenylbenzoxazole scaffold, here, we report the antibiotic effects of asymmetric analogs of this scaffold against a panel of bacteria known as the ESKAPE pathogens (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter species). While GroEL/ES inhibitors were largely ineffective against K pneumoniae, A. baumannii, P. aeruginosa, and E. cloacae (Gram-negative bacteria), many analogs were potent inhibitors of E. faecium and S. aureus proliferation (Gram-positive bacteria, EC50 values of the most potent analogs were in the 1-2 mu M range). Furthermore, even though some compounds inhibit human HSP60/10 biochemical functions in vitro (IC50 values in the 1-10 mu M range), many of these exhibited moderate to low cytotoxicity to human liver and kidney cells (CC50 values > 20 mu M).

  DOI：

  10.1021/acs.jmedchem.8b00989