1-(4-chlorophenyl)-5-ethoxy-3-phenyl-1H-pyrazole | 1147771-12-7

• 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-ethoxy-3-phenyl-1H-pyrazole
• 英文别名: 1-(4-Chlorophenyl)-5-ethoxy-3-phenylpyrazole
• CAS: 1147771-12-7
• 化学式: C₁₇H₁₅ClN₂O
• 分子量: 298.772
• InChiKey: VXIZXQIUUORRHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-5-ethoxy-3-phenyl-1H-pyrazole 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 36.0h， 以86%的产率得到1-(4-氯苯基)-3-苯基-2-吡唑-5-酮
  参考文献：
  名称：

  Alkoxypyrazoles and the process for their preparation

  摘要：

  本发明涉及一种烷氧基吡唑的制备方法，以及新的烷氧基吡唑化合物。

  公开号：

  EP2151433A1
• 作为产物：
  描述：

  3(5)-ethoxy-5(3)-phenyl-1H-pyrazole 、 对氯碘苯 在 copper(I) oxide 、 N,N'-bis(2-pyridylmethylidene)-1,2-(RS,RS)-cyclohexanediamine 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以15%的产率得到1-(4-chlorophenyl)-3-ethoxy-5-phenyl-1H-pyrazole
  参考文献：
  名称：

  N-arylation of 3-alkoxypyrazoles, the case of the pyridines

  摘要：

  In the course of a research program focused on the preparation of libraries of new chemical entities derived from 3-alkoxypyrazoles, we studied their N-pyridylation using 2, 3 or 4-bromopyridines This was achieved using Cristau and Taillefer copper-catalyzed arylation method and mostly led to the 3-alkoxy-1H-pyrazol-1-yl pyridine isomer along with lesser amount of the alternative 5-alkoxy-1H-pyrazol-1-yl pyridine The structures of these isomers were often established via their chemical tansformations and sometimes recourse to unambiguous synthetic routes for comparison purposes The alternative use of 2-fluoropyridine-based arylation was also investigated and lifted some of the limitations encountered in the course of this study (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.02.032

文献信息

• 1,3‐diarylpyrazolones as potential anticancer agents for non‐small cell lung cancer: Synthesis and antiproliferative activity evaluation
  作者：Achyut Dahal、Mary Lo、Sitanshu Singh、Huu Vo、Denzel ElHage、Seetharama D. Jois、Siva Murru

  DOI：10.1111/cbdd.14030

  日期：2022.4

  The cell cycle analysis showed that the compound P7 and P11 arrests the cell cycle at G0/G1 phase, whereas the compounds P13 and P14 involved in G2/M phase arrest. The results from antiproliferative activity screening, cell cycle analysis, and kinase profiling indicate that the suitably substituted 1,3-diarylpyrazolones exhibit high antiproliferative activity against non-small cell lung cancer cells

  使用微波辅助方法合成了一系列具有不同取代模式的吡唑啉酮化合物，并评估了它们对人肺腺癌细胞系（A549 和 NCI-H522）的体外抗增殖活性。在测试的化合物中，吡唑啉酮 P7 对 A549 和 NCIH522 癌细胞系均表现出高抗增殖活性，同时对非癌细胞的细胞毒性低 10 倍。此外，与临床批准的药物阿法替尼和吉非替尼相比，我们的化合物 P7 和 P11 对 A549 和 NCIH522 细胞表现出更高的抗增殖活性和选择性。细胞周期分析显示化合物P7和P11使细胞周期停滞在G0/G1期，而化合物P13和P14参与G2/M期停滞。抗增殖活性筛选的结果，
• Nitrogen's reactivity of various 3-alkoxypyrazoles
  作者：Sandrine Guillou、Frédéric J. Bonhomme、Yves L. Janin

  DOI：10.1016/j.tet.2009.01.099

  日期：2009.3

  Our current interest in the design of original chemical libraries featuring a pyrazole nucleus led us to focus on the chemistry of the 3-alkoxy-5-methylpyrazoles we have recently made readily available. With in mind the preparation of an array of the less accessible 1-arylpyrazol-3-ones, the present report describes the respective nitrogen's reactivity of various 3-alkoxypyrazoles toward arylation reaction, using arylboronic acids, as well as alkylation reactions using methyl iodide or benzylbromide. The structure assignments of the isomers obtained were achieved using long distance N-15-H-1 NMR correlation measurements or by the recourse to unambiguous synthetic pathways. (c) 2009 Elsevier Ltd. All rights reserved.