N-(3,5-Difluoro-4-hydroxyphenyl)benzenesulfonamide | 1028354-40-6

• 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-(3,5-Difluoro-4-hydroxyphenyl)benzenesulfonamide
• CAS: 1028354-40-6
• 化学式: C₁₂H₉F₂NO₃S
• 分子量: 285.271
• InChiKey: YAWFBTGILXVPSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(3,5-Difluoro-4-hydroxyphenyl)benzenesulfonamide 、 苯甲酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 以73.4%的产率得到2,6-difluoro-4-(phenylsulfonamido)phenyl benzoate
  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
• 作为产物：
  描述：

  在 水 作用下， 反应 2.0h， 以225 mg的产率得到N-(3,5-Difluoro-4-hydroxyphenyl)benzenesulfonamide
  参考文献：
  名称：

  N-（3,5-二氟-4-羟基苯基）苯磺酰胺作为醛糖还原酶抑制剂的设计与合成。

  摘要：

  制备N-（3，5-二氟-4-羟基苯基）苯磺酰胺（4）及其衍生物5-7作为先前报道的醛糖还原酶抑制剂的假定生物等排体，所述抑制剂是N-苯磺酰基甘氨酸衍生物I-IV。所制备的化合物的体外醛糖还原酶抑制活性高于相应的甘氨酸衍生物。此外，母体化合物4显示出高的抗氧化潜能。另外，确定肠通透性为4，并且有初步证据表明存在有效的内流机制。总体而言，数据表明，所提出的化学型可以作为设计推定药物治疗剂的核心结构，旨在解决糖尿病的长期并发症。

  DOI：

  10.1016/j.bmc.2008.01.042

文献信息

• Design and synthesis of N-(3,5-difluoro-4-hydroxyphenyl)benzenesulfonamides as aldose reductase inhibitors
  作者：Polyxeni Alexiou、Ioannis Nicolaou、Milan Stefek、Albin Kristl、Vassilis J. Demopoulos

  DOI：10.1016/j.bmc.2008.01.042

  日期：2008.4.1

  N-(3,5-Difluoro-4-hydroxyphenyl)benzenesulfonamide (4) and its derivatives 5-7 were prepared as putative bioisosteres of the previously reported aldose reductase inhibitors, which are the N-benzenesulfonylglycine derivatives I-IV. The in vitro aldose reductase inhibitory activity of the prepared compounds is higher than that of the respective glycine derivatives. Furthermore, the parent compound 4

  制备N-（3，5-二氟-4-羟基苯基）苯磺酰胺（4）及其衍生物5-7作为先前报道的醛糖还原酶抑制剂的假定生物等排体，所述抑制剂是N-苯磺酰基甘氨酸衍生物I-IV。所制备的化合物的体外醛糖还原酶抑制活性高于相应的甘氨酸衍生物。此外，母体化合物4显示出高的抗氧化潜能。另外，确定肠通透性为4，并且有初步证据表明存在有效的内流机制。总体而言，数据表明，所提出的化学型可以作为设计推定药物治疗剂的核心结构，旨在解决糖尿病的长期并发症。
• A Diverse Series of Substituted Benzenesulfonamides as Aldose Reductase Inhibitors with Antioxidant Activity: Design, Synthesis, and in Vitro Activity
  作者：Polyxeni Alexiou、Vassilis J. Demopoulos

  DOI：10.1021/jm101008m

  日期：2010.11.11

  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).