2-(3-(4-bromophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazole | 1246443-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-(4-bromophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazole
• 英文别名: 2-phenyl-5-[1-phenyl-3-(4-bromophenyl)-4-pyrazolyl]-1,3,4-oxadiazole；2-[3-(4-Bromophenyl)-1-phenylpyrazol-4-yl]-5-phenyl-1,3,4-oxadiazole
• CAS: 1246443-86-6
• 化学式: C₂₃H₁₅BrN₄O
• 分子量: 443.302
• InChiKey: SRGMIYFCNZNNBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-溴苯乙酮苯腙 在 碘苯二乙酸 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 11.5h， 生成 2-(3-(4-bromophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Design and synthesis of novel 2-phenyl-5-(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazoles as selective COX-2 inhibitors with potent anti-inflammatory activity

  摘要：

  A novel series of 2-phenyl-5-(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazoles were designed and synthesized for selective COX-2 inhibition with potent anti-inflammatory activity. Among the compounds tested, 9g (2-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazole) was found to be the most potent inhibitor of COX-2 with IC50 of 0.31 μM showing promising degree of anti-inflammatory activity in the carrageenan-induced rat paw edema model with ED50 of 74.3 mg/kg. The lead compound 9g further showed suppression of acetic acid-induced writhes comparable to that of aspirin and gastro-sparing profile superior to the aspirin. Molecular docking analysis displayed higher binding affinity of ligands towards COX-2 than COX-1.

  DOI：

  10.1016/j.ejmech.2014.04.045

文献信息

• Hypervalent iodine(III) mediated synthesis of novel unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles as antibacterial and antifungal agents
  作者：Om Prakash、Manoj Kumar、Rajesh Kumar、Chetan Sharma、K.R. Aneja

  DOI：10.1016/j.ejmech.2010.06.023

  日期：2010.9

  A series of novel 2,5-disubstituted 1,3,4-oxadiazoles 4 have been conveniently synthesized by oxidative cyclization of pyrazolylaldehyde N-acylhydrazones 3 promoted by iodobenzene diacetate under mild conditions (11 examples, up to 92% isolated yields). All the eleven compounds were tested in vitro for their antibacterial activity against Gram-positive bacteria namely, Staphylococcus aureus, Bacillus

  通过在温和条件下由碘代苯二乙酸酯促进的吡唑基醛N-酰基hydr酮3的氧化环化反应，可以方便地合成一系列新颖的2,5-二取代的1,3,4-恶二唑4（11个实例，分离产率高达92％）。在体外测试了所有这11种化合物对革兰氏阳性菌，即金黄色葡萄球菌，枯草芽孢杆菌和两种革兰氏阴性菌，即大肠杆菌和铜绿假单胞菌的抗菌活性。还测试了所有合成的化合物对两种真菌的抑制作用。
• Design and synthesis of novel 2-phenyl-5-(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazoles as selective COX-2 inhibitors with potent anti-inflammatory activity
  作者：Sumit Bansal、Manju Bala、Sharad Kumar Suthar、Shivani Choudhary、Shoumyo Bhattacharya、Varun Bhardwaj、Sumit Singla、Alex Joseph

  DOI：10.1016/j.ejmech.2014.04.045

  日期：2014.6

  A novel series of 2-phenyl-5-(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazoles were designed and synthesized for selective COX-2 inhibition with potent anti-inflammatory activity. Among the compounds tested, 9g (2-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazole) was found to be the most potent inhibitor of COX-2 with IC50 of 0.31 μM showing promising degree of anti-inflammatory activity in the carrageenan-induced rat paw edema model with ED50 of 74.3 mg/kg. The lead compound 9g further showed suppression of acetic acid-induced writhes comparable to that of aspirin and gastro-sparing profile superior to the aspirin. Molecular docking analysis displayed higher binding affinity of ligands towards COX-2 than COX-1.