4-(2-propylidenehydrazinyl)benzoic acid

• 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-(2-propylidenehydrazinyl)benzoic acid
• 英文别名: 4-(2-Propylidenehydrazinyl)benzoic acid
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: MEIRYZJDUTZIAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-propylidenehydrazinyl)benzoic acid 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 5.0h， 生成 4-(4-methyl-1H-pyrazole-1-yl)benzoic acid
  参考文献：
  名称：

  Modeling molecular interactions of propounded pyrazole based drug candidates against bacterial DNA gyrase: Validation by syntheses and biological studies

  摘要：

  A class of nitrogen-based heterocycles, pyrazoles and their derivatives, are cardinal agents in the field of pharmacology. Here, we have conducted in silico studies on newly designed pyrazole based drug molecules, thereby revealing their activities and interaction behaviors when docked against S. aureus DNA gyrase upon comparison with a standard drug ciprofloxacin and previously reported few compounds. The drug likeliness of the compounds was analyzed using QikProp module of Maestro 11.5 (Schrodinger) through ADME (Absorption, Distribution, Metabolism and Excretion) analysis. Among the predicted compounds, we have synthesized four pyrazole derivatives; namely 5-(3, 5-dimethyl-1H-pyrazol-1-yl) 1,3-benzoic acid, 5-(3, 5-dimethyl-1H-pyrazol-1-yl) 1,3-benzenedicarboxylic acid, 4-(4-methyl-1H-pyrazole-1-yl) benzoic acid and 1-(4-carboxyphenyl)-1H-pyrazole-4-carboxylic acid. All the four compounds are characterized by H-1 and C-13 NMR, IR, UV, and mass spectrophotometry. We have successfully tested the same compounds for anti-microbial activities involving testing with standard bacterial as well as fungal strains. Anti-bacterial activity testing was performed against two Gram-positive bacteria: Staphylococcus aureus, Bacillus subtilis and three Gram-negative bacteria: Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica. Anti-fungal activity was carried out against a well-known fungal strain Candida albicans. The observed antimicrobial activities are in well agreement with the docking results. The DFT study was also carried out to compare the conformational stability of the optimized structures and docked-pose of the four molecules. (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2019.05.125
• 作为产物：
  描述：

  4-肼基苯甲酸 、 正丁醛 以 乙醇 为溶剂， 反应 4.0h， 以88%的产率得到4-(2-propylidenehydrazinyl)benzoic acid
  参考文献：
  名称：

  Modeling molecular interactions of propounded pyrazole based drug candidates against bacterial DNA gyrase: Validation by syntheses and biological studies

  摘要：

  A class of nitrogen-based heterocycles, pyrazoles and their derivatives, are cardinal agents in the field of pharmacology. Here, we have conducted in silico studies on newly designed pyrazole based drug molecules, thereby revealing their activities and interaction behaviors when docked against S. aureus DNA gyrase upon comparison with a standard drug ciprofloxacin and previously reported few compounds. The drug likeliness of the compounds was analyzed using QikProp module of Maestro 11.5 (Schrodinger) through ADME (Absorption, Distribution, Metabolism and Excretion) analysis. Among the predicted compounds, we have synthesized four pyrazole derivatives; namely 5-(3, 5-dimethyl-1H-pyrazol-1-yl) 1,3-benzoic acid, 5-(3, 5-dimethyl-1H-pyrazol-1-yl) 1,3-benzenedicarboxylic acid, 4-(4-methyl-1H-pyrazole-1-yl) benzoic acid and 1-(4-carboxyphenyl)-1H-pyrazole-4-carboxylic acid. All the four compounds are characterized by H-1 and C-13 NMR, IR, UV, and mass spectrophotometry. We have successfully tested the same compounds for anti-microbial activities involving testing with standard bacterial as well as fungal strains. Anti-bacterial activity testing was performed against two Gram-positive bacteria: Staphylococcus aureus, Bacillus subtilis and three Gram-negative bacteria: Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica. Anti-fungal activity was carried out against a well-known fungal strain Candida albicans. The observed antimicrobial activities are in well agreement with the docking results. The DFT study was also carried out to compare the conformational stability of the optimized structures and docked-pose of the four molecules. (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2019.05.125

文献信息

• Modeling molecular interactions of propounded pyrazole based drug candidates against bacterial DNA gyrase: Validation by syntheses and biological studies
  作者：Shubhangi、Nikhil Kumar、Rajendiran Kanagaraj、Kashmiri Lal、Avijit Kumar Paul

  DOI：10.1016/j.molstruc.2019.05.125

  日期：2019.11

  A class of nitrogen-based heterocycles, pyrazoles and their derivatives, are cardinal agents in the field of pharmacology. Here, we have conducted in silico studies on newly designed pyrazole based drug molecules, thereby revealing their activities and interaction behaviors when docked against S. aureus DNA gyrase upon comparison with a standard drug ciprofloxacin and previously reported few compounds. The drug likeliness of the compounds was analyzed using QikProp module of Maestro 11.5 (Schrodinger) through ADME (Absorption, Distribution, Metabolism and Excretion) analysis. Among the predicted compounds, we have synthesized four pyrazole derivatives; namely 5-(3, 5-dimethyl-1H-pyrazol-1-yl) 1,3-benzoic acid, 5-(3, 5-dimethyl-1H-pyrazol-1-yl) 1,3-benzenedicarboxylic acid, 4-(4-methyl-1H-pyrazole-1-yl) benzoic acid and 1-(4-carboxyphenyl)-1H-pyrazole-4-carboxylic acid. All the four compounds are characterized by H-1 and C-13 NMR, IR, UV, and mass spectrophotometry. We have successfully tested the same compounds for anti-microbial activities involving testing with standard bacterial as well as fungal strains. Anti-bacterial activity testing was performed against two Gram-positive bacteria: Staphylococcus aureus, Bacillus subtilis and three Gram-negative bacteria: Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica. Anti-fungal activity was carried out against a well-known fungal strain Candida albicans. The observed antimicrobial activities are in well agreement with the docking results. The DFT study was also carried out to compare the conformational stability of the optimized structures and docked-pose of the four molecules. (C) 2019 Elsevier B.V. All rights reserved.