tert-butyl (1-(2,3,5,6-tetrafluoro-4-sulfamoylphenyl)-1H-1,2,3-triazol-4-yl)methylcarbamate | 1613267-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl (1-(2,3,5,6-tetrafluoro-4-sulfamoylphenyl)-1H-1,2,3-triazol-4-yl)methylcarbamate
• 英文别名: tert-butyl N-[[1-(2,3,5,6-tetrafluoro-4-sulfamoylphenyl)triazol-4-yl]methyl]carbamate
• CAS: 1613267-03-0
• 化学式: C₁₄H₁₅F₄N₅O₄S
• 分子量: 425.364
• InChiKey: JNDHGMUYOOCXJU-UHFFFAOYSA-N

物化性质

• 熔点：
  137-138 °C
• 密度：
  1.630±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  tert-butyl (1-(2,3,5,6-tetrafluoro-4-sulfamoylphenyl)-1H-1,2,3-triazol-4-yl)methylcarbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以80%的产率得到4-(4-(aminomethyl)-1H-1,2,3-triazol-1-yl)-2,3,5,6-tetrafluorobenzenesulfonamide
  参考文献：
  名称：

  Carbonic Anhydrase Inhibition with Benzenesulfonamides and Tetrafluorobenzenesulfonamides Obtained via Click Chemistry

  摘要：

  A series of novel benzene- and 2,3,5,6-tetrafluorobenzenesulfonamide was synthesized by using a click chemistry approach starting from azido-substituted sulfonamides and alkynes, incorporating aryl, alkyl, cycloalkyl, and amino-/hydroxy-/halogenoalkyl moieties. The new compounds were medium potency inhibitors of the cytosolic carbonic anhydrase (CA, EC 4.2.1.1) isoforms I and II and low nanomolar/subnanomolar inhibitors of the tumor-associated hCA IX and XII isoforms. The X-ray crystal structure of two such sulfonamides in adduct with hCA II allowed us to understand the factors governing inhibitory power.

  DOI：

  10.1021/ml500196t
• 作为产物：
  描述：

  2,3,4,5,6-五氟苯磺酰氯 在 ammonium hydroxide 、 sodium azide 、 铜 、 三乙胺盐酸盐 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 68.0h， 生成 tert-butyl (1-(2,3,5,6-tetrafluoro-4-sulfamoylphenyl)-1H-1,2,3-triazol-4-yl)methylcarbamate
  参考文献：
  名称：

  Carbonic Anhydrase Inhibition with Benzenesulfonamides and Tetrafluorobenzenesulfonamides Obtained via Click Chemistry

  摘要：

  A series of novel benzene- and 2,3,5,6-tetrafluorobenzenesulfonamide was synthesized by using a click chemistry approach starting from azido-substituted sulfonamides and alkynes, incorporating aryl, alkyl, cycloalkyl, and amino-/hydroxy-/halogenoalkyl moieties. The new compounds were medium potency inhibitors of the cytosolic carbonic anhydrase (CA, EC 4.2.1.1) isoforms I and II and low nanomolar/subnanomolar inhibitors of the tumor-associated hCA IX and XII isoforms. The X-ray crystal structure of two such sulfonamides in adduct with hCA II allowed us to understand the factors governing inhibitory power.

  DOI：

  10.1021/ml500196t