1-(3-硝基苯基)-5-苯基吡唑-3,4-二羧酸 | 96723-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(3-硝基苯基)-5-苯基吡唑-3,4-二羧酸
• 英文名称: 1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3,4-dicarboxylic acid
• 英文别名: 1h-pyrazole-3,4-dicarboxylic Acid, 1-(3-nitrophenyl)-5-phenyl-；1-(3-nitrophenyl)-5-phenylpyrazole-3,4-dicarboxylic acid
• CAS: 96723-10-3
• 化学式: C₁₇H₁₁N₃O₆
• 分子量: 353.291
• InChiKey: YXDCWKHOLSPQLX-UHFFFAOYSA-N

物化性质

• 熔点：
  208 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  606.7±55.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 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：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3-硝基苯基)-5-苯基吡唑-3,4-二羧酸 在 氯化亚砜 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 11.0h， 生成 N³,N⁴-bis(methylcarbamoyl)-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3,4-dicarboxamide
  参考文献：
  名称：

  Synthesis, structure–activity relationships, and in vitro antibacterial and antifungal activity evaluations of novel pyrazole carboxylic and dicarboxylic acid derivatives

  摘要：

  A series of pyrazole-3-carboxylic acid and pyrazole-3,4-dicarboxylic acid derivatives were synthesized, the structures were confirmed by their NMR (H-1 and C-13) and FT-IR spectra, and elemental analyses. The antibacterial and antifungal activities of the compounds against five bacterial and five fungal pathogens were screened using modified agar well diffusion assay. Most of the molecules have inhibitory effects on both standard and clinical Candida albicans strains. However, only the molecules 8, 10, 21, and 22 demonstrate some inhibitory effects on Candida parapsilosis, Candida tropicalis, and Candida glabrata strains. The structure-antifungal activity relationships of the compounds on the C. albicans strains were investigated by electron-conformational method. The pharmacophores and antipharmacophores responsible for the inhibition and non-inhibition of the C. albicans strains were obtained by electronic and geometrical characteristics of the reactive fragments of the molecules. These fragments along with the associated parameters can be used in designing the future more potent antifungal agents. It has been shown that both the positions of electronegative atoms like F and O in the pyrazole substituents and the amount of the associated charges on such atoms are crucial in regulating the strength of antifungal activity for the C. albicans strain. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.033
• 作为产物：
  描述：

  [(3-硝基苯基)肼基]氯乙酸乙酯 在 sodium hydroxide 、 sodium ethanolate 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 50.0h， 生成 1-(3-硝基苯基)-5-苯基吡唑-3,4-二羧酸
  参考文献：
  名称：

  Cocco; Maccioni; Plumitallo, Farmaco, Edizione Scientifica, 1985, vol. 40, # 4, p. 272 - 284

  摘要：

  DOI：

文献信息

• The synthesis of novel pyrazole-3,4-dicarboxamides bearing 5-amino-1,3,4-thiadiazole-2-sulfonamide moiety with effective inhibitory activity against the isoforms of human cytosolic carbonic anhydrase I and II
  作者：Samet Mert、Zuhal Alım、Mehmet Mustafa İşgör、Şükrü Beydemir、Rahmi Kasımoğulları

  DOI：10.1016/j.bioorg.2016.07.006

  日期：2016.10

  A series of 1-(3-substituted-phenyl)-5-phenyl-N(3),N(4)-bis(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3,4-dicarboxamides (4-15) were synthesized. The structures of these pyrazole-sulfonamides were confirmed by FT-IR, (1)H NMR, (13)C NMR and elemental analysis methods. Human cytosolic carbonic anhydrase (CA, EC 4.2.1.1) isozymes (hCA I and II) were purified from erythrocyte cells by affinity chromatography

  一系列1-（3-取代的苯基）-5-苯基-N（3），N（4）-双（5-氨磺酰基-1,3,4-噻二唑-2-基）-1H-吡唑-合成了3，4-二羧酸酰胺（4-15）。这些吡唑磺酰胺的结构通过FT-IR，（1）H NMR，（13）C NMR和元素分析法确认。通过亲和色谱法从红细胞中纯化人胞质碳酸酐酶（CA，EC 4.2.1.1）同工酶（hCA I和II）。在体外研究了新合成的衍生物（4-15）对这些同工酶的酯酶活性的抑制作用。hCA I的Ki值确定为0.119-3.999μM，hCA II的Ki值确定为0.084-0.878μM。结果表明，针对hCA I的化合物6和针对hCA II的化合物11具有最高的抑制作用。除此之外，化合物8对两种同工酶的抑制作用最低。
• COCCO, M. T.;MACCIONI, A.;PLUMITALLO, A., FARMACO. ED. SCI., 1985, 40, N 4, 272-284
  作者：COCCO, M. T.、MACCIONI, A.、PLUMITALLO, A.

  DOI：——

  日期：——
• Cocco; Maccioni; Plumitallo, Farmaco, Edizione Scientifica, 1985, vol. 40, # 4, p. 272 - 284
  作者：Cocco、Maccioni、Plumitallo

  DOI：——

  日期：——
• Synthesis, structure–activity relationships, and in vitro antibacterial and antifungal activity evaluations of novel pyrazole carboxylic and dicarboxylic acid derivatives
  作者：Samet Mert、Rahmi Kasımoğulları、Tuba İça、Ferdağ Çolak、Ahmet Altun、Salim Ok

  DOI：10.1016/j.ejmech.2014.03.033

  日期：2014.5

  A series of pyrazole-3-carboxylic acid and pyrazole-3,4-dicarboxylic acid derivatives were synthesized, the structures were confirmed by their NMR (H-1 and C-13) and FT-IR spectra, and elemental analyses. The antibacterial and antifungal activities of the compounds against five bacterial and five fungal pathogens were screened using modified agar well diffusion assay. Most of the molecules have inhibitory effects on both standard and clinical Candida albicans strains. However, only the molecules 8, 10, 21, and 22 demonstrate some inhibitory effects on Candida parapsilosis, Candida tropicalis, and Candida glabrata strains. The structure-antifungal activity relationships of the compounds on the C. albicans strains were investigated by electron-conformational method. The pharmacophores and antipharmacophores responsible for the inhibition and non-inhibition of the C. albicans strains were obtained by electronic and geometrical characteristics of the reactive fragments of the molecules. These fragments along with the associated parameters can be used in designing the future more potent antifungal agents. It has been shown that both the positions of electronegative atoms like F and O in the pyrazole substituents and the amount of the associated charges on such atoms are crucial in regulating the strength of antifungal activity for the C. albicans strain. (C) 2014 Elsevier Masson SAS. All rights reserved.