1-[4-(aminosulfonyl)phenyl]-3-(4-nitrophenyl)-1H-pyrazole-4-carboxylic acid | 1293980-89-8

• 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-(aminosulfonyl)phenyl]-3-(4-nitrophenyl)-1H-pyrazole-4-carboxylic acid
• 英文别名: 3-(4-Nitrophenyl)-1-(4-sulfamoylphenyl)pyrazole-4-carboxylic acid
• CAS: 1293980-89-8
• 化学式: C₁₆H₁₂N₄O₆S
• 分子量: 388.36
• InChiKey: MUSGUKZLVUYEHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  170
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[4-(aminosulfonyl)phenyl]-3-(4-nitrophenyl)-1H-pyrazole-4-carboxylic acid 在 硫酸 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 生成 4-[4-(hydrazinocarbonyl)-3-(4-nitrophenyl)-1H-pyrazole-1-yl]benzenesulfonamide
  参考文献：
  名称：

  4-Functionalized 1,3-diarylpyrazoles bearing benzenesulfonamide moiety as selective potent inhibitors of the tumor associated carbonic anhydrase isoforms IX and XII

  摘要：

  A library of 4-functionalized 1,3-diarylpyrazoles (3a-3h, 5a-5g and 6a-6g) was designed, synthesized and evaluated against four human carbonic anhydrase (CA, EC 4.2.1.1) isozymes representing two cytosolic isozymes hCA I and hCA II, and two transmembrane tumor associated ones, hCA IX and hCA XII. All the twenty two tested compounds exhibited excellent CA activity profile against the four CA isozymes when compared to the reference drug acetazolamide. Six of the tested compounds (3a-3b, 3f, 3h, 6a and 6b) displayed low nanomolar affinity (K-i < 5 nM) for hCA IX whereas seven compounds (3a-3b, 3d-3f, 3h and 6f) displayed K-i < 10 nM against hCA XII. In addition, they acted as selective CA inhibitors of isoforms IX and XII over the physiological isoforms I and II. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.023
• 作为产物：
  描述：

  对硝基苯乙酮 在 吡啶 、 甲醇 、 potassium permanganate 、 sodium acetate 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.5h， 生成 1-[4-(aminosulfonyl)phenyl]-3-(4-nitrophenyl)-1H-pyrazole-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of some 4-functionalized-pyrazoles as antimicrobial agents

  摘要：

  1,3-Diaryl-4-formylpyrazoles 8 bearing benzenesulfonamide moiety at position-1 were synthesized as important intermediates following Vilsmeier-Haack strategy. Aldehyde moiety of 4-formylpyrazole was then converted into carboxylic acid 9, cyano 10 and carbothioamide 11 using established procedures. Out of these 4-functionalized pyrazoles, pyrazole-4-carboxylic acids 9 and carbothioamides 11 were evaluated for their in vitro antibacterial activity against four pathogenic bacterial strains namely, Staphylococcus aureus, Bacillus subtilis (Gram-positive), Escherichia coli, Pseudomonas aeruginosa (Gram-negative), and in vitro antifungal activity against two pathogenic fungal strains namely, Aspergillus niger and Aspergillus flavus. Three tested compounds, 9e, 11b and 11f exhibited moderate antibacterial activity against Gram-positive bacteria and 9g showed moderate antifungal activity against the tested fungi. However, none of the compounds showed any activity against Gram-negative bacteria. (c) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.060

文献信息

• Synthesis and biological evaluation of some 4-functionalized-pyrazoles as antimicrobial agents
  作者：Pawan K. Sharma、Navneet Chandak、Pawan Kumar、Chetan Sharma、Kamal R. Aneja

  DOI：10.1016/j.ejmech.2011.01.060

  日期：2011.4

  1,3-Diaryl-4-formylpyrazoles 8 bearing benzenesulfonamide moiety at position-1 were synthesized as important intermediates following Vilsmeier-Haack strategy. Aldehyde moiety of 4-formylpyrazole was then converted into carboxylic acid 9, cyano 10 and carbothioamide 11 using established procedures. Out of these 4-functionalized pyrazoles, pyrazole-4-carboxylic acids 9 and carbothioamides 11 were evaluated for their in vitro antibacterial activity against four pathogenic bacterial strains namely, Staphylococcus aureus, Bacillus subtilis (Gram-positive), Escherichia coli, Pseudomonas aeruginosa (Gram-negative), and in vitro antifungal activity against two pathogenic fungal strains namely, Aspergillus niger and Aspergillus flavus. Three tested compounds, 9e, 11b and 11f exhibited moderate antibacterial activity against Gram-positive bacteria and 9g showed moderate antifungal activity against the tested fungi. However, none of the compounds showed any activity against Gram-negative bacteria. (c) 2011 Elsevier Masson SAS. All rights reserved.
• 4-Functionalized 1,3-diarylpyrazoles bearing benzenesulfonamide moiety as selective potent inhibitors of the tumor associated carbonic anhydrase isoforms IX and XII
  作者：Poonam Khloya、Gulsah Celik、SitaRam、Daniela Vullo、Claudiu T. Supuran、Pawan K. Sharma

  DOI：10.1016/j.ejmech.2014.02.023

  日期：2014.4

  A library of 4-functionalized 1,3-diarylpyrazoles (3a-3h, 5a-5g and 6a-6g) was designed, synthesized and evaluated against four human carbonic anhydrase (CA, EC 4.2.1.1) isozymes representing two cytosolic isozymes hCA I and hCA II, and two transmembrane tumor associated ones, hCA IX and hCA XII. All the twenty two tested compounds exhibited excellent CA activity profile against the four CA isozymes when compared to the reference drug acetazolamide. Six of the tested compounds (3a-3b, 3f, 3h, 6a and 6b) displayed low nanomolar affinity (K-i < 5 nM) for hCA IX whereas seven compounds (3a-3b, 3d-3f, 3h and 6f) displayed K-i < 10 nM against hCA XII. In addition, they acted as selective CA inhibitors of isoforms IX and XII over the physiological isoforms I and II. (C) 2014 Elsevier Masson SAS. All rights reserved.