4-苯甲酰基-1-(4-硝基苯基)-5-苯基-1H-吡唑-3-羧酸 | 658081-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-苯甲酰基-1-(4-硝基苯基)-5-苯基-1H-吡唑-3-羧酸
• 英文名称: 4-benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid
• 英文别名: 4-benzoyl-1-(4-nitro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid；4-Benzoyl-1-(4-nitro-phenyl)-5-phenyl-1H-pyrazol-3-carbonsaeure；4-benzoyl-1-(4-nitrophenyl)-5-phenylpyrazole-3-carboxylic acid
• CAS: 658081-76-6
• 化学式: C₂₃H₁₅N₃O₅
• 分子量: 413.389
• InChiKey: QSNNXEPLGZMQNP-UHFFFAOYSA-N

物化性质

• 熔点：
  210 °C (decomp)(Solv: ethanol (64-17-5))
• 沸点：
  708.0±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-苯甲酰基-1-(4-硝基苯基)-5-苯基-1H-吡唑-3-羧酸 在 吡啶 、 氯化亚砜 作用下， 反应 3.0h， 生成 butyl 4-benzoyl-1-[4-nitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Ilhan, Ilhan Özer; Bahadir, Özlem; Önal, Zülbiye, Asian Journal of Chemistry, 2012, vol. 24, # 1, p. 141 - 144

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 4-benzoyl-1-[4-nitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylate 在 氢氧化钾 作用下， 生成 4-苯甲酰基-1-(4-硝基苯基)-5-苯基-1H-吡唑-3-羧酸
  参考文献：
  名称：

  Fusco, Gazzetta Chimica Italiana, 1939, vol. 69, p. 344,349

  摘要：

  DOI：

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。
• Synthesis of novel pyrazole-4-carboxylates by rearrangement reaction: Experimental and theoretical characterization
  作者：Elif Korkusuz、Yusuf Sert、Ertan Şahin、İsmail Yıldırım、İrfan Koca

  DOI：10.1016/j.jpcs.2023.111536

  日期：2023.10

  pyrazole-4-carboxylate compounds (5a-d) were synthesized from the esterification reaction of pyrazole-5-carboxylic acid compound by rearrangement. Molecules 5a-d have been studied in detail both experimentally (x-ray, FT-IR and NMR) and theoretically. Optimization of the structure for all compounds, Highest Occupied Molecular Orbital (HOMO)-Lowest Unoccupied Molecular Orbital (LUMO) values and distributions

  本研究通过吡唑-5-羧酸化合物的酯化反应，通过重排合成了吡唑-4-羧酸烷基酯化合物( 5a-d )。分子5a-d已通过实验（X 射线、FT-IR 和 NMR）和理论进行了详细研究。通过DFT理论对所有化合物的结构进行了优化，最高占据分子轨道（HOMO）-最低未占据分子轨道（LUMO）值和分布以及仅5d（最稳定能量和单晶）的分子静电势（MEP ）分析在 B3LYP 函数和 6–311++G(d,p) 基组上。结构可能结晶（5d）通过赫什菲尔德表面分析从实验晶体中得到。在下一步中，通过分子对接计算得出5a、5b、5c和5d分子之间的相互作用，以及根据相似性提出的分子和目标分子。然后，研究了药物相似性和 ADME 特性。
• 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：——
• 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.
• Synthesis of 5-amino-1,3,4-thiadiazole-2-sulphonamide derivatives and their inhibition effects on human carbonic anhydrase isozymes
  作者：Rahmi Kasımoğulları、Metin Bülbül、Samet Mert、Hülya Güleryüz

  DOI：10.3109/14756366.2010.491795

  日期：2011.4.1

  In this study, some novel inhibitors were synthesised from the further stage reactions of 4-benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carbonyl chloride with 5-amino-1,3,4-thiadiazole-2-sulphonamide 1 (inhibitor 1). They were characterised by elemental and spectral (