2-[5-(4-methoxyphenyl)-3-phenyl-1H-pyrazol-1-yl]pyridine | 1062682-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-[5-(4-methoxyphenyl)-3-phenyl-1H-pyrazol-1-yl]pyridine
• 英文别名: 2-[5-(4-Methoxyphenyl)-3-phenylpyrazol-1-yl]pyridine
• CAS: 1062682-30-7
• 化学式: C₂₁H₁₇N₃O
• 分子量: 327.385
• InChiKey: DNBRRFZDWPOBQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲酸甲酯 、 对甲氧基苯乙酮 在 sodium hydride 作用下， 以 乙醇 、 甲苯 、 mineral oil 为溶剂， 反应 6.0h， 生成 2-[5-(4-methoxyphenyl)-3-phenyl-1H-pyrazol-1-yl]pyridine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel pyrazole derivatives with anticancer activity

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2011.08.014

文献信息

• Electronic effects in the reaction of 1,3-diaryl-1,3-diketones with hydrazinopyridines
  作者：Nathan C. Duncan、Charles M. Garner、Tim Nguyen、Fernando Hung、Kevin Klausmeyer

  DOI：10.1016/j.tetlet.2008.07.104

  日期：2008.9

  The regioselectivity of the condensation of electronically unsymmetrical 1,3-diaryl- 1,3-diketones with 2-hydrazinopyridine and 2,6-bis-hydrazinopyridine to form N-(2-pyridyl)-3,5-diarylpyrazoles was studied. Significant electronic effects on regioselectivities were observed, and regioselectivities were opposite to those exhibited by perfluoroalkyl/alkyl 1,3-diketones. The electronic effects correlate well to the difference between the Hammett sigma(+) coefficients of the para substituents on the aryl rings. (C) 2008 Elsevier Ltd. All rights reserved.