1-甲基-3-(对甲苯基)-1H-吡唑-4-甲醛 | 304477-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-甲基-3-(对甲苯基)-1H-吡唑-4-甲醛
• 中文别名: 1-甲基-3-对甲苯-1H-吡唑-4-甲醛
• 英文名称: 1-methyl-3-(p-tolyl)-1H-pyrazole-4-carbaldehyde
• 英文别名: 1-methyl-3-(4-methylphenyl)pyrazole-4-carbaldehyde
• CAS: 304477-41-6
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: IBUHXEBPFFEKQS-UHFFFAOYSA-N

物化性质

• 沸点：
  365.3±30.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-甲基-3-(对甲苯基)-1H-吡唑-4-甲醛 在 三氯氧磷 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 (2E)-2-(dimethylhydrazinylidene)-2-[1-methyl-3-(4-methylphenyl)pyrazol-4-yl]acetaldehyde
  参考文献：
  名称：

  Aza-enamines X:Formylation of Pyrazole-4-carbaldehydeHydrazones at the Hydrazonoazomethine C-Atom

  摘要：

  1,3-双取代的1H-吡唑-4-甲醛-N,N-二甲基脲1与Vilsmeier-Haack试剂反应，符合氮杂烯胺概念，通过在偶氮甲碱C原子上的亲电取代反应生成了1,4,5-三氮杂戊二烯盐2。这些产物经水解得到2-腙基-2-(1H-吡唑-4-基)乙醛3。亲电攻击并未发生在吡唑的乙烯相似位点5′上。

  DOI：

  10.1055/s-2003-40527
• 作为产物：
  描述：

  对甲基苯乙酮 在 sodium acetate 、 potassium carbonate 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-甲基-3-(对甲苯基)-1H-吡唑-4-甲醛
  参考文献：
  名称：

  Synthesis and the interaction of 2-(1 H -pyrazol-4-yl)-1 H -imidazo[4,5-f][1,10]phenanthrolines with telomeric DNA as lung cancer inhibitors

  摘要：

  A novel series of 2-(1H-pyrazol-4-y1)-1H-imidazo[4,5-f][1,101phenanthrolines were designed, synthesized and evaluated for their antitumor activity against lung adenocarcinoma by CCK-8 assay, electrophoretic mobility shift assay (EMSA), UV-melting study, wound healing assay and docking study. These compounds showed good inhibitory activities against lung adenocarcinoma. Especially compound 12c exhibited potential antiproliferative activity against A549 cell line with the half maximal inhibitory concentration (IC50) value of 1.48 mu M, which was a more potent inhibitor than cisplatin (IC50 = 12.08 mu M) and leading compound 2 (IC50 = 1.69 mu M), and the maximum cell inhibitory rate being up to 98.40%. Moreover, further experiments demonstrated that compounds 12a-d can strongly interact with telomeric DNA to stabilize G-quadruplex DNA with increased am values from 12.44 to 20.54 degrees C at a ratio of DNA to compound 1:10. These results implied that growth inhibition of A549 cells mediated by these phenanthroline derivatives is possibly positively correlated to the fact their interaction with telomeric G-quadruplexs. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.030

文献信息

• Brehme; Gruendemann; Schneider, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 7, p. 700 - 706
  作者：Brehme、Gruendemann、Schneider

  DOI：——

  日期：——
• Aza-enamines X:Formylation of Pyrazole-4-carbaldehydeHydrazones at the Hydrazonoazomethine C-Atom
  作者：R. Brehme、E. Gründemann、M. Schneider、R. Radeglia、G. Reck、B. Schulz

  DOI：10.1055/s-2003-40527

  日期：——

  1,3-Disubstituted 1H-pyrazole-4-carbaldehyde-N,N-di­methylhydrazones 1 reacted with the Vilsmeier-Haack reagent, corresponding to the aza-enamine concept, in an electrophilic substitution reaction at the azomethine C-atom yielding the 1,4,5-triaza-pentadienium salts 2. These were hydrolysed to give 2-hydrazono-2-(1H-pyrazole-4-yl)ethanals 3. The electrophilic attack did not take place at the vinylogous position 5′ of the pyrazoles.

  1,3-双取代的1H-吡唑-4-甲醛-N,N-二甲基脲1与Vilsmeier-Haack试剂反应，符合氮杂烯胺概念，通过在偶氮甲碱C原子上的亲电取代反应生成了1,4,5-三氮杂戊二烯盐2。这些产物经水解得到2-腙基-2-(1H-吡唑-4-基)乙醛3。亲电攻击并未发生在吡唑的乙烯相似位点5′上。
• Synthesis and the interaction of 2-(1 H -pyrazol-4-yl)-1 H -imidazo[4,5-f][1,10]phenanthrolines with telomeric DNA as lung cancer inhibitors
  作者：Jiachun Liu、Mei Chen、Yanli Wang、Xiaoyin Zhao、Sijia Wang、Yanling Wu、Wen Zhang

  DOI：10.1016/j.ejmech.2017.03.030

  日期：2017.6

  A novel series of 2-(1H-pyrazol-4-y1)-1H-imidazo[4,5-f][1,101phenanthrolines were designed, synthesized and evaluated for their antitumor activity against lung adenocarcinoma by CCK-8 assay, electrophoretic mobility shift assay (EMSA), UV-melting study, wound healing assay and docking study. These compounds showed good inhibitory activities against lung adenocarcinoma. Especially compound 12c exhibited potential antiproliferative activity against A549 cell line with the half maximal inhibitory concentration (IC50) value of 1.48 mu M, which was a more potent inhibitor than cisplatin (IC50 = 12.08 mu M) and leading compound 2 (IC50 = 1.69 mu M), and the maximum cell inhibitory rate being up to 98.40%. Moreover, further experiments demonstrated that compounds 12a-d can strongly interact with telomeric DNA to stabilize G-quadruplex DNA with increased am values from 12.44 to 20.54 degrees C at a ratio of DNA to compound 1:10. These results implied that growth inhibition of A549 cells mediated by these phenanthroline derivatives is possibly positively correlated to the fact their interaction with telomeric G-quadruplexs. (C) 2017 Elsevier Masson SAS. All rights reserved.