4,4,4-trifluoro-3-hydroxy-1-(2-chloro-pyridin-4-yl)but-2-en-1-one | 1131479-13-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4,4-trifluoro-3-hydroxy-1-(2-chloro-pyridin-4-yl)but-2-en-1-one
• CAS: 1131479-13-4
• 化学式: C₉H₅ClF₃NO₂
• 分子量: 251.592
• InChiKey: DNVUWMAABDTMID-UHFFFAOYSA-N

物化性质

• 沸点：
  357.9±42.0 °C(predicted)
• 密度：
  1.511±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  50.19
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4,4,4-trifluoro-3-hydroxy-1-(2-chloro-pyridin-4-yl)but-2-en-1-one 、 4-(甲基磺酰基)苯肼盐酸盐 以 乙醇 、 水 为溶剂， 反应 20.0h， 以40%的产率得到1-(4-methanesulfonylphenyl)-5-(2-chloropyridin-4-yl)-3-trifluoromethyl-1H-pyrazole
  参考文献：
  名称：

  Synthesis of Celecoxib Analogues Possessing a N-Difluoromethyl-1,2-dihydropyrid-2-one 5-Lipoxygenase Pharmacophore: Biological Evaluation as Dual Inhibitors of Cyclooxygenases and 5-Lipoxygenase with Anti-Inflammatory Activity

  摘要：

  A novel class of 1-(4-methanesulfonylphenyl and 4-aminosulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazole hybrid cyclooxygenase-2 (COX-2)/5-lipoxygenase (5-LOX) inhibitory anti-inflammatory agents was designed. Replacement of the tolyl ring present in celecoxib by the N-difluoromethyl-1,2-dihydropyrid-2-one moiety provided compounds showing dual selective COX-2/5-LOX inhibitory activities. 1-(4-Aminosulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazole exhibited good anti-inflammatory (AI) activity (ED50 = 27.7 mg/kg po) that compares favorably with the reference drugs celecoxib ED50 = 10.8 mg/kg po) and ibuprofen (ED50 = 67.4 mg/kg po). The N-difluoromethyl-1,2-dihydropyridin-2-one moiety provides a novel 5-LOX pharmacophore for the design of cyclic hydroxamic mimetics for exploitation in the development of COX-2/5-LOX inhibitory AI drugs.

  DOI：

  10.1021/jm8015188
• 作为产物：
  描述：

  2-氯-4-乙酰吡啶 、 三氟乙酸乙酯 在 sodium methylate 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以91%的产率得到4,4,4-trifluoro-3-hydroxy-1-(2-chloro-pyridin-4-yl)but-2-en-1-one
  参考文献：
  名称：

  Synthesis of Celecoxib Analogues Possessing a N-Difluoromethyl-1,2-dihydropyrid-2-one 5-Lipoxygenase Pharmacophore: Biological Evaluation as Dual Inhibitors of Cyclooxygenases and 5-Lipoxygenase with Anti-Inflammatory Activity

  摘要：

  A novel class of 1-(4-methanesulfonylphenyl and 4-aminosulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazole hybrid cyclooxygenase-2 (COX-2)/5-lipoxygenase (5-LOX) inhibitory anti-inflammatory agents was designed. Replacement of the tolyl ring present in celecoxib by the N-difluoromethyl-1,2-dihydropyrid-2-one moiety provided compounds showing dual selective COX-2/5-LOX inhibitory activities. 1-(4-Aminosulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazole exhibited good anti-inflammatory (AI) activity (ED50 = 27.7 mg/kg po) that compares favorably with the reference drugs celecoxib ED50 = 10.8 mg/kg po) and ibuprofen (ED50 = 67.4 mg/kg po). The N-difluoromethyl-1,2-dihydropyridin-2-one moiety provides a novel 5-LOX pharmacophore for the design of cyclic hydroxamic mimetics for exploitation in the development of COX-2/5-LOX inhibitory AI drugs.

  DOI：

  10.1021/jm8015188