1-(4-fluorophenyl)-3-trifluoromethyl-5-(3-methyl-2-oxo-3H-benzoxazol-6-yl)-1H-pyrazole | 1245624-24-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-fluorophenyl)-3-trifluoromethyl-5-(3-methyl-2-oxo-3H-benzoxazol-6-yl)-1H-pyrazole
• 英文别名: 1-(4-Fluorophenyl)-3-trifluoromethyl-5-(3-methyl-2-oxo-3H-benzoxazole-6-yl)-1H-pyrazole；6-[2-(4-fluorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]-3-methyl-1,3-benzoxazol-2-one
• CAS: 1245624-24-1
• 化学式: C₁₈H₁₁F₄N₃O₂
• 分子量: 377.298
• InChiKey: YKOUXSMVMVBXAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4,4,4-trifluoro-1-(3-methyl-2-oxo-3H-benzoxazol-6-yl)-1,3-dioxobutane 、 4-氟苯肼盐酸盐 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 以51%的产率得到1-(4-fluorophenyl)-3-trifluoromethyl-5-(3-methyl-2-oxo-3H-benzoxazol-6-yl)-1H-pyrazole
  参考文献：
  名称：

  Synthesis, biological evaluation, and docking studies of novel heterocyclic diaryl compounds as selective COX-2 inhibitors

  摘要：

  Three novel series of diaryl heterocyclic derivatives bearing the 2-oxo-5H-furan, 2-oxo-3H-1,3-oxazole, and 1H-pyrazole moieties as the central heterocyclic ring were synthesized and their in vitro inhibitory activities on COX-1 and COX-2 isoforms were evaluated using a purified enzyme assay. The 2-oxo-5H-furan derivative 6b was identified as potent COX inhibitor with selectivity toward COX-1 (COX-1 IC(50) = 0.061 mu M and COX-2 IC(50) = 0.325 mu M; selectivity index (SI) = 0.19). Among the 1H-pyrazole derivatives, 11b was found to be a potent COX-2 inhibitor, about 38 times more potent than Rofecoxib (COX-2 IC(50) = 0.011 mu M and 0.398 mu M, respectively), but showed no selectivity for COX-2 isoform. Compound 11c demonstrated strong and selective COX-2 inhibitory activity (COX-1 IC(50) = 1 mu M, COX-2 IC(50) = 0.011 mu M; SI = similar to 92). Molecular docking studies of compounds 6b and 11b-d into the binding sites of COX-1 and COX-2 allowed to shed light on the binding mode of these novel COX inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.009