(1-phenyl-5-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)methyl 2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (1-phenyl-5-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)methyl 2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetate
• 英文别名: [1-Phenyl-5-[3-(trifluoromethyl)phenyl]pyrazol-3-yl]methyl 2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyacetate；[1-phenyl-5-[3-(trifluoromethyl)phenyl]pyrazol-3-yl]methyl 2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyacetate
• 化学式: C₃₄H₂₃F₃N₂O₆
• 分子量: 612.562
• InChiKey: BARPDUKYWMOMPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  99.9
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  间三氟甲基苯乙酮 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 sodium methylate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (1-phenyl-5-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)methyl 2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetate
  参考文献：
  名称：

  Design and biological evaluation of novel hybrids of 1, 5-diarylpyrazole and Chrysin for selective COX-2 inhibition

  摘要：

  The overexpress of COX-2 was clearly associated with carcinogenesis and COX-2 as a possible target has long been exploited for cancer therapy. In this work, we described the design and synthesis of a series of diarylpyrazole derivatives integrating with chrysin. Among them, compound e9 exhibited the most potent inhibitory activity against COX-2 and antiproliferative activity against Hela cells with IC50 value of 1.12 mu M. Further investigation revealed that e9 could induce apoptosis of Hela cells by mitochondrial depolarization and block the G1 phase of cell cycle in a dose-dependent manner. Besides, molecular docking simulation results was further confirmed that e9 could bind well with COX-2. In summary, compound e9 may be promising candidates for cancer therapy.

  DOI：

  10.1016/j.bmc.2018.07.022

文献信息

• Design and biological evaluation of novel hybrids of 1, 5-diarylpyrazole and Chrysin for selective COX-2 inhibition
  作者：Shen-Zhen Ren、Zhong-Chang Wang、Xiao-Hua Zhu、Dan Zhu、Zhang Li、Fa-Qian Shen、Yong-Tao Duan、Han Cao、Jing Zhao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2018.07.022

  日期：2018.8

  The overexpress of COX-2 was clearly associated with carcinogenesis and COX-2 as a possible target has long been exploited for cancer therapy. In this work, we described the design and synthesis of a series of diarylpyrazole derivatives integrating with chrysin. Among them, compound e9 exhibited the most potent inhibitory activity against COX-2 and antiproliferative activity against Hela cells with IC50 value of 1.12 mu M. Further investigation revealed that e9 could induce apoptosis of Hela cells by mitochondrial depolarization and block the G1 phase of cell cycle in a dose-dependent manner. Besides, molecular docking simulation results was further confirmed that e9 could bind well with COX-2. In summary, compound e9 may be promising candidates for cancer therapy.