5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylic acid methyl ester | 318238-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylic acid methyl ester
• 英文别名: methyl 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylate；methyl 5-(4-chlorophenyl)-1-phenylpyrazole-3-carboxylate
• CAS: 318238-06-1
• 化学式: C₁₇H₁₃ClN₂O₂
• 分子量: 312.755
• InChiKey: GJDZDAKNWSTVBE-UHFFFAOYSA-N

物化性质

• 沸点：
  476.0±35.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 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 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (5-(4-chlorophenyl)-1-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
• 作为产物：
  描述：

  对氯苯乙酮 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylic acid methyl ester
  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

• When Aryldiazonium Salts Meet Vinyl Diazoacetates: A Cobalt-Catalyzed Regiospecific Synthesis of <i>N</i>-Arylpyrazoles
  作者：Haiheng Guo、Daming Zhang、Chenghao Zhu、Jian Li、Guangyang Xu、Jiangtao Sun

  DOI：10.1021/ol5012339

  日期：2014.6.6

  A cobalt-catalyzed C-N bond formation between aryl diazonium salts and vinyl diazoacetates has been developed under relatively mild conditions. The N-arylpyrazoles have been prepared in moderate to high yields in a regiospecific way.