(Z)-5-((3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-dione | 1346173-83-8

• 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-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[[3-(4-fluorophenyl)-1-phenylpyrazol-4-yl]methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1346173-83-8
• 化学式: C₁₉H₁₂FN₃O₂S
• 分子量: 365.388
• InChiKey: JTRQGOJQBJHGRJ-YBEGLDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  5

反应信息

• 作为产物：
  描述：

  1-(1-(4-fluorophenyl)ethylidene)-2-phenylhydrazine 在 哌啶 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 8.5h， 生成 (Z)-5-((3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-dione
  参考文献：
  名称：

  新型二芳基取代吡唑基噻唑烷二酮类作为有效的胰腺脂肪酶抑制剂的设计，合成，生物学评估和分子模型研究

  摘要：

  通过合适的吡唑甲醛与2,4-噻唑烷二酮（TZD）和硝基苄基取代的2,4-噻唑烷二酮的反应合成了一系列新颖的二芳基取代的吡唑基2,4-噻唑烷二酮。体外筛选所得化合物的胰腺脂肪酶（PL）抑制活性。分别使用对硝基苯基丁酸酯和三丁酸甘油酯作为底物，进行了两种测定方案，即方法A和B。 与标准药物奥利司他具有可比的标准药物奥利司他（IC 50  = 0.99 µM和X i50），化合物11e表现出有效的PL抑制活性（方法A和B中的IC 50  = 4.81 µM和X i50 = 10.01）。 = 3.72）。在TZD的N-3位上硝基苄基的存在和在吡唑环的C-3位上苯环对位的取代基的性质显着影响了所测试化合物的PL抑制活性。酶抑制动力学的11e揭示了其可逆的竞争抑制作用，类似于奥利司他。分子对接研究证实了药效学设计的原理，并且与体外结果一致。化合物11e表现出-153.349kcal / mol的潜在

  DOI：

  10.1016/j.bmcl.2017.06.069

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.
• Design, synthesis, biological evaluation and molecular modelling studies of novel diaryl substituted pyrazolyl thiazolidinediones as potent pancreatic lipase inhibitors
  作者：Sridhar S.N.C.、Deendyal Bhurta、Dharmvir Kantiwal、Ginson George、Vikramdeep Monga、Atish T. Paul

  DOI：10.1016/j.bmcl.2017.06.069

  日期：2017.8

  exhibited a potential MolDock score of −153.349 kcal/mol. Further, the diaryl pyrazolyl wing exhibited hydrophobic interactions with the amino acids of the hydrophobic lid domain. Moreover, the carbonyl group at 2nd position of the TZD ring existed adjacent to Ser 152 (≈3 Å) similar to that of orlistat. A 10 ns molecular dynamics simulation of 11e–PL complex revealed a stable binding conformation of 11e

  通过合适的吡唑甲醛与2,4-噻唑烷二酮（TZD）和硝基苄基取代的2,4-噻唑烷二酮的反应合成了一系列新颖的二芳基取代的吡唑基2,4-噻唑烷二酮。体外筛选所得化合物的胰腺脂肪酶（PL）抑制活性。分别使用对硝基苯基丁酸酯和三丁酸甘油酯作为底物，进行了两种测定方案，即方法A和B。 与标准药物奥利司他具有可比的标准药物奥利司他（IC 50  = 0.99 µM和X i50），化合物11e表现出有效的PL抑制活性（方法A和B中的IC 50  = 4.81 µM和X i50 = 10.01）。 = 3.72）。在TZD的N-3位上硝基苄基的存在和在吡唑环的C-3位上苯环对位的取代基的性质显着影响了所测试化合物的PL抑制活性。酶抑制动力学的11e揭示了其可逆的竞争抑制作用，类似于奥利司他。分子对接研究证实了药效学设计的原理，并且与体外结果一致。化合物11e表现出-153.349kcal / mol的潜在