3-Fluoro-4-[5-(4-methoxy-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-benzenesulfonamide | 606126-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Fluoro-4-[5-(4-methoxy-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-benzenesulfonamide
• 英文别名: 3-fluoro-4-[5-(4-methoxyphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
• CAS: 606126-05-0
• 化学式: C₁₇H₁₃F₄N₃O₃S
• 分子量: 415.368
• InChiKey: OHIVDQMFQYBGDC-UHFFFAOYSA-N

物化性质

• 熔点：
  116-120 °C
• 沸点：
  550.8±60.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  丁酸酐 、 3-Fluoro-4-[5-(4-methoxy-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-benzenesulfonamide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以100%的产率得到N1-butyryl-3-fluoro-4-[5-(4-methoxyphenyl)-3-trifluoromethyl-1H-1-pyrazolyl]-1-benzenesulfonamide
  参考文献：
  名称：

  Synthesis and Cyclooxygenase-2 Inhibiting Property of 1,5-Diarylpyrazoles with Substituted Benzenesulfonamide Moiety as Pharmacophore:  Preparation of Sodium Salt for Injectable Formulation^†

  摘要：

  A series of 1,5-diarylpyrazoles having a substituted benzenesulfonamide moiety as pharmacophore was synthesized and evaluated for cyclooxygenase (COX-1/COX-2) inhibitory activities. Through SAR and molecular modeling, it was found that fluorine substitution on the benzenesulfonamide moiety along with an electron-donating group at the 4-position of the 5-aryl ring yielded selectivity as well as potency for COX-2 inhibition in vitro. Among such compounds 3-fluoro-4-[5-(4-methoxyphenyl)-3-trifluoromethyl-1H-1-pyrazolyl]-1-benzenesulfonamide 3 displayed interesting pharmacokinetic properties along with antiinflammatory activity in vivo. Among the sodium salts tested in vivo, 10, the propionyl analogue of 3, showed excellent antiinflammatory activity and therefore represents a new lead structure for the development of injectable COX-2 specific inhibitors.

  DOI：

  10.1021/jm020563g
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.17h， 生成 3-Fluoro-4-[5-(4-methoxy-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-benzenesulfonamide
  参考文献：
  名称：

  Synthesis and Cyclooxygenase-2 Inhibiting Property of 1,5-Diarylpyrazoles with Substituted Benzenesulfonamide Moiety as Pharmacophore:  Preparation of Sodium Salt for Injectable Formulation^†

  摘要：

  A series of 1,5-diarylpyrazoles having a substituted benzenesulfonamide moiety as pharmacophore was synthesized and evaluated for cyclooxygenase (COX-1/COX-2) inhibitory activities. Through SAR and molecular modeling, it was found that fluorine substitution on the benzenesulfonamide moiety along with an electron-donating group at the 4-position of the 5-aryl ring yielded selectivity as well as potency for COX-2 inhibition in vitro. Among such compounds 3-fluoro-4-[5-(4-methoxyphenyl)-3-trifluoromethyl-1H-1-pyrazolyl]-1-benzenesulfonamide 3 displayed interesting pharmacokinetic properties along with antiinflammatory activity in vivo. Among the sodium salts tested in vivo, 10, the propionyl analogue of 3, showed excellent antiinflammatory activity and therefore represents a new lead structure for the development of injectable COX-2 specific inhibitors.

  DOI：

  10.1021/jm020563g