N-(3,5-difluoro-4-hydroxyphenyl)-4-(1H-pyrrol-1-yl)benzenesulfonamide | 1025960-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-(3,5-difluoro-4-hydroxyphenyl)-4-(1H-pyrrol-1-yl)benzenesulfonamide
• 英文别名: N-(3,5-difluoro-4-hydroxyphenyl)-4-pyrrol-1-ylbenzenesulfonamide
• CAS: 1025960-74-0
• 化学式: C₁₆H₁₂F₂N₂O₃S
• 分子量: 350.346
• InChiKey: IIVMKWGKQROOKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 4-Amino-N-(3,5-difluoro-4-hydroxyphenyl)benzenesulfonamide 在 4-氯吡啶盐酸盐 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以70%的产率得到N-(3,5-difluoro-4-hydroxyphenyl)-4-(1H-pyrrol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  A Diverse Series of Substituted Benzenesulfonamides as Aldose Reductase Inhibitors with Antioxidant Activity: Design, Synthesis, and in Vitro Activity

  摘要：

  We have previously reported the successful replacement of a carboxylic acid functionality with that of a difluorophenolic group on the known aldose reductase inhibitors (ARIs) of 2-(phenylsulfonamido)-acetic acid chemotype. In the present work, based on bioisosteric principles, additional 2,6-difluorophenol and tetrazole, methylsulfonylamide, and isoxazolidin-3-one phenylsulfonamide derivatives were synthesized and tested in vitro in protocols primarily related to the long-term diabetic complications. Most of the compounds were found as ARIs at IC50 < 100 mu M, while the introduction of the 4-bromo-2-fluorobenzyl group in a phenylsulfonamidodifluorophenol structure resulted in a compound (4c) presenting a submicromolar inhibitory profile. However, the derivatives of tetrazole, methylsulfonylamine, and the (R)-enantiomer of isoxazolidin-3-one did not exhibit appreciable A R activity. The selectivity of the active A R Is is also discussed. Furthermore, the synthesized compounds exhibited potent antioxidant potential (homogeneous and heterogeneous systems).

  DOI：

  10.1021/jm101008m