4-benzoyl-1-[4-nitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylic acid chloride | 658081-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-benzoyl-1-[4-nitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylic acid chloride
• 英文别名: 4-Benzoyl-1-(4-nitrophenyl)-5-phenyl-1h-pyrazole-3-carbonyl chloride；4-benzoyl-1-(4-nitrophenyl)-5-phenylpyrazole-3-carbonyl chloride
• CAS: 658081-82-4
• 化学式: C₂₃H₁₄ClN₃O₄
• 分子量: 431.835
• InChiKey: KDPWHUKAUJBFIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-benzoyl-1-[4-nitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylic acid chloride 在 氨 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 以70%的产率得到4-benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  环状草酰化合物与肼或Hy反应的研究。2. 4-苄基-1-（4-硝基苯基）-5-苯基-1H-吡唑-3-羧酸的合成与反应

  摘要：

  DOI：

  10.1023/b:cohc.0000046695.00178.79
• 作为产物：
  描述：

  4-benzoyl-5-phenyl-furan-2,3-dione 在 氯化亚砜 作用下， 反应 6.25h， 生成 4-benzoyl-1-[4-nitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylic acid chloride
  参考文献：
  名称：

  环状草酰化合物与肼或Hy反应的研究。2. 4-苄基-1-（4-硝基苯基）-5-苯基-1H-吡唑-3-羧酸的合成与反应

  摘要：

  DOI：

  10.1023/b:cohc.0000046695.00178.79

文献信息

• Functionalization Reactions of Various Pyrazole-3-carboxylic Acid Chlorides with Some Ureas
  作者：Ilhan Özer Ilhan、Kazim Demirkol、Zülbiye Önal、Senem Akkoç、Mehmet Çadir

  DOI：10.14233/ajchem.2014.16000

  日期：——

  The 1H-pyrazole-3-carboxylic acids 2 or their remarkably stable acid chlorides 3 can easily be converted into the corresponding 1H-pyrazole-3-carbonyl-N-urea derivatives (5a-k) from reaction with urea nucleophiles. It has been demonstrated that with the variation in reaction conditions, the reaction changes thus leading to different products. All newly synthesized compounds were characterized by elemental analysis, FT-IR, 1H and 13C NMR spectral data. All compounds were compared with their previous analogues.

  1H-吡唑-3-羧酸2或其非常稳定的酸氯化物3可以很方便地通过与尿素核素的反应转化为相应的1H-吡唑-3-羰基-N-脲衍生物（5a-k）。已经证明，在反应条件变化的情况下，反应会发生变化，从而导致不同的产物。所有新合成的化合物均通过元素分析、FT-IR、1H和13C NMR光谱数据进行表征。所有化合物均与其先前的类似物进行了比较。
• Ilhan, Ilhan ÖZer; ÇAdir, Mehmet, Asian Journal of Chemistry, 2013, vol. 25, # 3, p. 1647 - 1650
  作者：Ilhan, Ilhan ÖZer、ÇAdir, Mehmet

  DOI：——

  日期：——
• Lhan, Ozer; Zuehal, Sevgi; Oenal, Zuelbiye, Heterocyclic Communications, 2009, vol. 15, # 4, p. 279 - 284
  作者：Lhan, Ozer、Zuehal, Sevgi、Oenal, Zuelbiye、Saripinar, Emin

  DOI：——

  日期：——
• Ilhan, Ilhan Özer; Bahadir, Özlem; Önal, Zülbiye, Asian Journal of Chemistry, 2012, vol. 24, # 1, p. 141 - 144
  作者：Ilhan, Ilhan Özer、Bahadir, Özlem、Önal, Zülbiye、Saripinar, Emin

  DOI：——

  日期：——
• Effects of new 5-amino-1,3,4-thiadiazole-2-sulfonamide derivatives on human carbonic anhydrase isozymes
  作者：Rahmi Kasımoğulları、Metin Bülbül、Hatice Günhan、Hülya Güleryüz

  DOI：10.1016/j.bmc.2009.03.048

  日期：2009.5

  Pyrazole carboxylic acid amides of 5-amino-1,3,4-thiadiazole-2-sulfonamide 1 (inhibitor 1) were synthesized from 4-benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carbonyl chloride and 4-benzoyl-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carbonyl chloride compounds. Human carbonic anhydrase isoenzymes (hCA-I and hCA-II) were purified from erythrocyte cells by the affinity chromatography. The inhibitory effects of inhibitor 1, acetazolamide (AAZ), and of 16 newly synthesized amides (8-11, 12a-f, 13a-c, 14a-b, and 15) on hydratase and esterase activities of these isoenzymes have been studied in vitro. The average IC50 values of the new compounds (8-11,12a-f, 13a-c, 14a-b, and 15) for hydratase activity ranged from 3.25 to 4.75 mu M for hCA-I and from 0.055 to 2.6 mu M for hCA-II. The mean IC50 values of the same inhibitors for esterase activity were in the range of 2.7-6.6 mu M for hCA-I ( with the exception of inhibitor 10, which did not inhibit the esterase activity of hCA-I) and of 0.013-4.2 mu M for hCA-II. The K-i values for new compounds (8-11, 12a-f, 13a-c, 14a-b, and 15) were observed well below that of the parent compound inhibitor 1 and were also comparable to that of AAZ under the same experimental conditions. The comparison of newly synthesized amides to inhibitor 1 and to AAZ indicated that the new derivatives preferentially inhibit hCA-II and are more potent inhibitors of hCA-II than the parent inhibitor 1 and AAZ. (C) 2009 Elsevier Ltd. All rights reserved.