3-(4-nitrophenyl)-1-phenyl-1H-pyrazole-4-carboxylic acid | 77169-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-nitrophenyl)-1-phenyl-1H-pyrazole-4-carboxylic acid
• 英文别名: 1-Phenyl-3-p-nitrophenylpyrazol-4-carbonsaeure；3-(4-Nitrophenyl)-1-phenylpyrazole-4-carboxylic acid
• CAS: 77169-13-2
• 化学式: C₁₆H₁₁N₃O₄
• 分子量: 309.281
• InChiKey: JJCMFGBUKOOVHI-UHFFFAOYSA-N

物化性质

• 沸点：
  520.0±35.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对氯苯胺 、 3-(4-nitrophenyl)-1-phenyl-1H-pyrazole-4-carboxylic acid 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以83%的产率得到N-(4-chlorophenyl)-3-(4-nitrophenyl)-1-phenyl-1H-pyrazole-4-carboxamide
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular docking studies of N,1,3-triphenyl-1H-pyrazole-4-carboxamide derivatives as anticancer agents

  摘要：

  A series of N,1,3-triphenyl-1H-pyrazole-4-carboxamide derivatives have been designed, synthesized and evaluated for their potential antiproliferation activity and Aurora-A kinase inhibitory activity. Among all the compounds, compound 10e possessed the most potent biological activity against HCT116 and MCF-7 cell lines with IC50 values of 0.39 +/- 0.06 mu M and 0.46 +/- 0.04 mu M, respectively, which were comparable to the positive control. Compound 10e also exhibited significant Aurora-A kinase inhibitory activity (IC50 = 0.16 +/- 0.03 mu M). Docking simulation was performed to position compound 10e into the active site of Aurora-A kinase, in order to get the probable binding model for further study. The results of Westernblot assay demonstrated that compound 10e possessed good Aurora-A kinase inhibitory activity against HCT116. Based on the preliminary results, it is deduced that compound 10e with potent Aurora-A kinase inhibitory activity may be a potential anticancer agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.066
• 作为产物：
  描述：

  1-(4-nitro-phenyl)-ethanone-phenylhydrazone 在 sodium chlorite 、 氨基磺酸 、 三氯氧磷 作用下， 以 丙酮 为溶剂， 反应 11.0h， 生成 3-(4-nitrophenyl)-1-phenyl-1H-pyrazole-4-carboxylic acid
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular docking studies of N,1,3-triphenyl-1H-pyrazole-4-carboxamide derivatives as anticancer agents

  摘要：

  A series of N,1,3-triphenyl-1H-pyrazole-4-carboxamide derivatives have been designed, synthesized and evaluated for their potential antiproliferation activity and Aurora-A kinase inhibitory activity. Among all the compounds, compound 10e possessed the most potent biological activity against HCT116 and MCF-7 cell lines with IC50 values of 0.39 +/- 0.06 mu M and 0.46 +/- 0.04 mu M, respectively, which were comparable to the positive control. Compound 10e also exhibited significant Aurora-A kinase inhibitory activity (IC50 = 0.16 +/- 0.03 mu M). Docking simulation was performed to position compound 10e into the active site of Aurora-A kinase, in order to get the probable binding model for further study. The results of Westernblot assay demonstrated that compound 10e possessed good Aurora-A kinase inhibitory activity against HCT116. Based on the preliminary results, it is deduced that compound 10e with potent Aurora-A kinase inhibitory activity may be a potential anticancer agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.066

文献信息

• Intermediate products, methods for their preparation and use thereof
  申请人：Personal Chemistry i Uppsala AB

  公开号：EP1367045A1

  公开（公告）日：2003-12-03

  Novel solid supported intermediate products of the general formula coupled to a solid polymeric support through one or both of the R1 groups or through the R4 group which are suitable for synthesis of heterocyclic compounds are disclosed. Methods for preparing such intermediate products are also disclosed and also the use of the intermediate products in simple and fast methods on solid phase for synthesis of heterocycles.

  揭示了一种新型的固体支持中间产物，其一般公式为，通过R1基团中的一个或两个或通过R4基团与固体聚合物支持物耦合，适用于合成杂环化合物。还公开了制备这种中间产物的方法，以及在固相上简单快速地合成杂环化合物的方法中使用这些中间产物。
• [EN] INHIBITOR COMPOUNDS FOR MALE CONTRACEPTION<br/>[FR] COMPOSÉS INHIBITEURS POUR CONTRACEPTION MASCULINE
  申请人：UNIV WASHINGTON

  公开号：WO2020123855A1

  公开（公告）日：2020-06-18

  Pyrazole compounds and piperazine compounds that are inhibitors of ALDH1A1 and ALDH1A2 and methods for using the pyrazole compounds and piperazine compounds in male contraceptive compositions for preventing spermatogenesis.

  对ALDH1A1和ALDH1A2具有抑制作用的吡唑化合物和哌嗪化合物，以及使用这些吡唑化合物和哌嗪化合物在男性避孕组合物中防止精子生成的方法。
• INHIBITOR COMPOUNDS FOR MALE CONTRACEPTION
  申请人：University of Washington

  公开号：US20210332030A1

  公开（公告）日：2021-10-28

  Pyrazole compounds and piperazine compounds that are inhibitors of ALDH1A1 and ALDH1A2 and methods for using the pyrazole compounds and piperazine compounds in male contraceptive compositions for preventing spermatogenesis.
• US7019094B2
  申请人：——

  公开号：US7019094B2

  公开（公告）日：2006-03-28
• Synthesis, biological evaluation, and molecular docking studies of N,1,3-triphenyl-1H-pyrazole-4-carboxamide derivatives as anticancer agents
  作者：Xi Li、Xiang Lu、Man Xing、Xian-Hui Yang、Ting-Ting Zhao、Hai-Bin Gong、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2012.04.066

  日期：2012.6

  A series of N,1,3-triphenyl-1H-pyrazole-4-carboxamide derivatives have been designed, synthesized and evaluated for their potential antiproliferation activity and Aurora-A kinase inhibitory activity. Among all the compounds, compound 10e possessed the most potent biological activity against HCT116 and MCF-7 cell lines with IC50 values of 0.39 +/- 0.06 mu M and 0.46 +/- 0.04 mu M, respectively, which were comparable to the positive control. Compound 10e also exhibited significant Aurora-A kinase inhibitory activity (IC50 = 0.16 +/- 0.03 mu M). Docking simulation was performed to position compound 10e into the active site of Aurora-A kinase, in order to get the probable binding model for further study. The results of Westernblot assay demonstrated that compound 10e possessed good Aurora-A kinase inhibitory activity against HCT116. Based on the preliminary results, it is deduced that compound 10e with potent Aurora-A kinase inhibitory activity may be a potential anticancer agent. (C) 2012 Elsevier Ltd. All rights reserved.