3-bromomethyl-1-(4-trifluoromethoxyphenyl)-5-phenyl-1H-pyrazole | 781663-79-4

• 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-bromomethyl-1-(4-trifluoromethoxyphenyl)-5-phenyl-1H-pyrazole
• 英文别名: 3-(bromomethyl)-5-phenyl-1-[4-(trifluoromethoxy)phenyl]pyrazole
• CAS: 781663-79-4
• 化学式: C₁₇H₁₂BrF₃N₂O
• 分子量: 397.194
• InChiKey: BLVWYVCVZOBLGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  27.05
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(5-氟-3-羟基苯基)-4-甲氧基-3,4,5,6-四氢-2H-吡喃 、 3-bromomethyl-1-(4-trifluoromethoxyphenyl)-5-phenyl-1H-pyrazole 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以74%的产率得到1-(4-trifluoromethoxyphenyl)-3-[3-fluoro-5-(4-methoxytetrahydropyran-4-yl)phenoxymethyl]-5-phenyl-1H-pyrazole
  参考文献：
  名称：

  New COX-2/5-LOX Inhibitors:  Apoptosis-Inducing Agents Potentially Useful in Prostate Cancer Chemotherapy

  摘要：

  The arachidonic acid metabolizing enzymes cyclooxygenase-2 (COX-2) and lipoxygenases (LOXs) have been found to be implicated in a variety of cancers, including prostate cancer. To develop new therapeutic treatments, it therefore seemed interesting to design dual COX-2/5-LOX inhibitors. We report here the synthesis and in vitro pharmacological properties of diarylpyrazole derivatives that have in their structure key pharmacophoric elements to obtain optimal interaction with subsites of active pockets in both enzyme systems. Using a molecular modeling approach, a set of SAR data is proposed, highlighting the importance of the sulfonyl group of one of the aryl moieties in terms of proliferation inhibition and/or apoptosis induction.

  DOI：

  10.1021/jm0407761
• 作为产物：
  描述：

  ethyl 4-hydroxy-2-oxo-4-phenylbut-3-enoate 在 锂硼氢 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 90.5h， 生成 3-bromomethyl-1-(4-trifluoromethoxyphenyl)-5-phenyl-1H-pyrazole
  参考文献：
  名称：

  New COX-2/5-LOX Inhibitors:  Apoptosis-Inducing Agents Potentially Useful in Prostate Cancer Chemotherapy

  摘要：

  The arachidonic acid metabolizing enzymes cyclooxygenase-2 (COX-2) and lipoxygenases (LOXs) have been found to be implicated in a variety of cancers, including prostate cancer. To develop new therapeutic treatments, it therefore seemed interesting to design dual COX-2/5-LOX inhibitors. We report here the synthesis and in vitro pharmacological properties of diarylpyrazole derivatives that have in their structure key pharmacophoric elements to obtain optimal interaction with subsites of active pockets in both enzyme systems. Using a molecular modeling approach, a set of SAR data is proposed, highlighting the importance of the sulfonyl group of one of the aryl moieties in terms of proliferation inhibition and/or apoptosis induction.

  DOI：

  10.1021/jm0407761