4-(ethoxycarbonyl)-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid | 1152334-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(ethoxycarbonyl)-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid
• 英文别名: 4-ethoxycarbonyl-1-(3-nitrophenyl)-5-phenylpyrazole-3-carboxylic acid
• CAS: 1152334-07-0
• 化学式: C₁₉H₁₅N₃O₆
• 分子量: 381.345
• InChiKey: PPOKEFIXTRQRTR-UHFFFAOYSA-N

物化性质

• 沸点：
  628.7±55.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(ethoxycarbonyl)-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid 在 氯化亚砜 、 sodium hydroxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 水 为溶剂， 反应 11.0h， 生成 N³,N⁴-1-tris(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：

  ethyl 4,5-dioxo-2-phenyl-4,5-dihydrofuran-3-carboxylate 、 benzaldehyde 3-nitrophenylhydrazone 以 neat (no solvent) 为溶剂， 生成 4-(ethoxycarbonyl)-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  1-(3-硝基苯基)-5-苯基-3-((4-(三氟甲基)苯基)氨基甲酰基)-1H-吡唑-4-乙基的合成、光谱(FT-IR和NMR)、DFT和分子对接研究羧酸盐

  摘要：

  合成了含有三氟甲基的pyrazole-3-carboxamide衍生物，并通过FT-IR、1 H NMR、13 C NMR光谱法和元素分析验证了分子的结构(E3N5PC ) 。为了确定标题化合物的理论表征、光谱和电子特性，采用 B3LYP 方法进行 DFT 计算，其中 6-311 + +  G ( d , p) 基组已通过利用 Gaussian 09w 包程序进行。此外，VEDA 4xx 软件已被用于确定标题分子的振动频率和势能分布百分比。通过 NBO 计算分析有助于提高分子稳定性的药物分子的化学选择性和反应性。分子对接是找到标题分子与大麻素受体1的最佳匹配方向。

  DOI：

  10.1007/s11164-022-04681-1

文献信息

• 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.
• Kasimoʇullari, Rahmi; Maden, Makbule; Yaglioglu, Ayse Sahin, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 9, p. 1134 - 1139
  作者：Kasimoʇullari, Rahmi、Maden, Makbule、Yaglioglu, Ayse Sahin、Mert, Samet、Demirtaş, Ibrahim

  DOI：——

  日期：——
• Design, synthesis, characterization, and antiproliferative activity of novel pyrazole-3-carboxylic acid derivatives
  作者：Rahmi Kasımoğulları、Hamdiye Duran、Ayşe Şahin Yağlıoğlu、Samet Mert、İbrahim Demirtaş

  DOI：10.1007/s00706-015-1450-7

  日期：2015.10

  In this study several novel 4-substituted-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid derivatives were synthesized. The structures of these pyrazole-3-carboxylic acid derivatives were characterized by FT-IR, H-1 NMR, C-13 NMR, and elemental analysis methods. Synthesized molecules were screened to evaluate their antiproliferative activities against Vero (African green monkey kidney), C6 (rat brain tumor), and HeLa (human uterus carcinoma) cells as in vitro. The tests were carried out as dose-dependent assay starting from 100 to 500 mu g/cm(3). Ethyl 1-(3-nitrophenyl)-5-phenyl-3-(phenylcarbamoyl)-1H-pyrazole-4-carboxylate exhibited the highest performance against HeLa, Vero, and C6 cells among the synthesized derivatives. Also, it showed better antiproliferative activity compared with 5-fluorouracil (5-FU) against Vero cell. Two compounds showed moderate antiproliferative activities against C6 cell line when compared with 5-FU. Also moderate antiproliferative activities against Vero and HeLa cell lines were found.
• Synthesis, characterization and antiglaucoma activity of some novel pyrazole derivatives of 5-amino-1,3,4-thiadiazole-2-sulfonamide
  作者：Rahmi Kasımoğulları、Metin Bülbül、B. Seçkin Arslan、Başak Gökçe

  DOI：10.1016/j.ejmech.2010.07.041

  日期：2010.11

  Pyrazole carboxylic acid derivatives of 5-amino-1,3,4-thiadiazole-2-sulfonamide (inhibitor 1) were synthesized from ethyl 3-(chlorocarbonyl)-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-4-carboxylate compound. The inhibitory effects of inhibitor 1, acetazolamide (AAZ) and of 11 newly synthesized amides (5a-b, 6, 7a-g, and 8) on hydratase and esterase activities of carbonic anhydrase isoenzymes (hCA-I and hCA-II) have been studied in vitro. The comparison of newly synthesized amides to inhibitor 1 and to AAZ indicated that the new derivatives inhibit CA isoenzymes and they are more potent inhibitors than the parent inhibitor 1 and AAZ. (C) 2010 Elsevier Masson SAS. All rights reserved.