1-(4-chlorophenyl)-5-(4-methoxyphenyl)-1H-pyrazole | 1345865-36-2

• 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-chlorophenyl)-5-(4-methoxyphenyl)-1H-pyrazole
• 英文别名: 1-(4-Chlorophenyl)-5-(4-methoxyphenyl)pyrazole
• CAS: 1345865-36-2
• 化学式: C₁₆H₁₃ClN₂O
• 分子量: 284.745
• InChiKey: MMADDJLRSBWVDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲酸甲酯 在 titanium tetraisopropoxide 、 copper diacetate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.08h， 生成 1-(4-chlorophenyl)-5-(4-methoxyphenyl)-1H-pyrazole
  参考文献：
  名称：

  铜介导的环丙醇与芳基重氮盐的串联开环/环化反应：N-芳基吡唑的合成。

  摘要：

  公开了一种由容易获得的环丙醇和芳基重氮盐合成结构多样的N-芳基吡唑的通用方法。该反应在室温下在数分钟内以宽的底物范围和优异的区域选择性进行。

  DOI：

  10.1039/c9cc09657d

文献信息

• Synthesis and biological evaluation of novel pyrazole derivatives with anticancer activity
  作者：Alessandro Balbi、Maria Anzaldi、Chiara Macciò、Cinzia Aiello、Mauro Mazzei、Rosaria Gangemi、Patrizio Castagnola、Mariangela Miele、Camillo Rosano、Maurizio Viale

  DOI：10.1016/j.ejmech.2011.08.014

  日期：2011.11

  We synthesized thirty-six novel pyrazole derivatives and studied their antiproliferative activity in human ovarian adenocarcinoma A2780 cells, human lung carcinoma A549 cells, and murine P388 leukemia cells.Four of these substances were selected because of their higher antiproliferative activity and further analyses showed that they were all able to induce apoptosis, although to a different extent. The expression of p53 and p21(waf1), which induce apoptosis and cell cycle arrest, was evaluated by western blot analysis in cells treated with compound 12d.The analysis of the cell cycle showed that all the selected compounds cause a partial G2/M block and the formation of polyploid cells. Furthermore, the four selected compounds were tested for their interaction with the microtubular cytoskeletal system by docking analysis, tubulin polymerization assay and immunofluorescence staining, demonstrating that the compound 12d, unlike the other active derivatives, was able to significantly bind dimers of alpha- and beta-tubulin, probably causing a molecular distortion resulting in the disassembly of microtubules. (C) 2011 Elsevier Masson SAS. All rights reserved.