(Z)-5-((3-(4-bromophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-dione | 1346173-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (Z)-5-((3-(4-bromophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-dione
• 英文别名: (z)-5-((3-(4-Bromophenyl)-1-phenyl-1h-pyrazol-4-yl)methylene)thiazolidine-2,4-dione；(5Z)-5-[[3-(4-bromophenyl)-1-phenylpyrazol-4-yl]methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1346173-84-9
• 化学式: C₁₉H₁₂BrN₃O₂S
• 分子量: 426.293
• InChiKey: UBCLNWHGOWBBSI-YBEGLDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-溴苯乙酮苯腙 在 哌啶 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 (Z)-5-((3-(4-bromophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and antimicrobial activity of 5-((3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-diones

  摘要：

  A series of 5-((3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-diones was synthesized by Knoevenagel condensation of various 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehydes (1a-h) with thiazolidine-2,4-dione (2) in ethanol in the presence of piperidine. All compounds were screened for their in vitro antibacterial (Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Escherichia coli) activity and compared with the commercially available antibiotic, ciprofloxacin. All compounds showed good activity against gram-positive bacteria, however, none of the compounds were found to be effective against gram-negative bacteria. Compound 3g was found to be most potent member among all the compounds showing MIC of 16 mu g/ml against S. aureus and 32 mu g/ml against B. subtilis. All the synthesized compounds were also tested for their in vitro antifungal (Aspergillus niger and A. flavus) activity and compared with commercially available fluconazole. They showed excellent antifungal activity. Compounds 3b, 3e, 3f and 3g were active against both fungi showing more than 60% inhibition. Compound 3e was found to be superior to the reference drug.

  DOI：

  10.1007/s00044-011-9829-4

文献信息

• Synthesis and antimicrobial activity of 5-((3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-diones
  作者：Om Prakash、Deepak K. Aneja、Poonam Lohan、Khalid Hussain、Sanjiv Arora、Chetan Sharma、Kamal R. Aneja

  DOI：10.1007/s00044-011-9829-4

  日期：2012.10

  A series of 5-((3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-diones was synthesized by Knoevenagel condensation of various 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehydes (1a-h) with thiazolidine-2,4-dione (2) in ethanol in the presence of piperidine. All compounds were screened for their in vitro antibacterial (Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Escherichia coli) activity and compared with the commercially available antibiotic, ciprofloxacin. All compounds showed good activity against gram-positive bacteria, however, none of the compounds were found to be effective against gram-negative bacteria. Compound 3g was found to be most potent member among all the compounds showing MIC of 16 mu g/ml against S. aureus and 32 mu g/ml against B. subtilis. All the synthesized compounds were also tested for their in vitro antifungal (Aspergillus niger and A. flavus) activity and compared with commercially available fluconazole. They showed excellent antifungal activity. Compounds 3b, 3e, 3f and 3g were active against both fungi showing more than 60% inhibition. Compound 3e was found to be superior to the reference drug.