2-(2-nitrophenyl)-5-(pyridin-3-yl)-1,3,4-oxadiazole

• 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: 2-(2-nitrophenyl)-5-(pyridin-3-yl)-1,3,4-oxadiazole
• 英文别名: 3-[5-(2-Nitrophenyl)-1,3,4-oxadiazol-2-yl]pyridine；2-(2-nitrophenyl)-5-pyridin-3-yl-1,3,4-oxadiazole
• 化学式: C₁₃H₈N₄O₃
• 分子量: 268.232
• InChiKey: KEHHOBBTAUFUCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-吡啶甲酰肼 、 邻硝基苯甲酸 在 三氯氧磷 作用下， 反应 0.15h， 以96%的产率得到2-(2-nitrophenyl)-5-(pyridin-3-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Structure–activity relationships of tyrosinase inhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues

  摘要：

  Here the tyrosinase inhibition studies of library of 2,5-disubstituted-1,3,4-oxadiazoles have been reported and their structure-activity relationship (SAR) also have been discussed. The library of the oxadiazoles was synthesized under the microwave irradiation and was structures of these were characterized by different spectral techniques. From this study it could be concluded that for a better inhibition of tyrosinase, electronegative substitution is essential as most probably the active site of the enzyme contain some hydrophobic site and position is also very important for the inhibition purposes due to the conformational space. The electronegativity of the compounds is somewhat proportional to the inhibitory activity. The compound 3e (3 '-[5-(4 '-bromophenyl)-1,3,4-oxadiazol-2-yl]pyridine) exhibited most potent (IC50 = 2.18 mu M) inhibition against the enzyme tyrosinase which is more potent than the standard potent inhibitor L-mimosine IC50 = 3.68 mu M). This molecule can be the best candidate as a lead compound for further development of drug for the treatments of several skin disorders. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.012

文献信息

• Structure–activity relationships of tyrosinase inhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues
  作者：Mahmud Tareq Hassan Khan、Muhammad Iqbal Choudhary、Khalid Mohammed Khan、Mubeen Rani、Atta-ur-Rahman

  DOI：10.1016/j.bmc.2005.03.012

  日期：2005.5

  Here the tyrosinase inhibition studies of library of 2,5-disubstituted-1,3,4-oxadiazoles have been reported and their structure-activity relationship (SAR) also have been discussed. The library of the oxadiazoles was synthesized under the microwave irradiation and was structures of these were characterized by different spectral techniques. From this study it could be concluded that for a better inhibition of tyrosinase, electronegative substitution is essential as most probably the active site of the enzyme contain some hydrophobic site and position is also very important for the inhibition purposes due to the conformational space. The electronegativity of the compounds is somewhat proportional to the inhibitory activity. The compound 3e (3 '-[5-(4 '-bromophenyl)-1,3,4-oxadiazol-2-yl]pyridine) exhibited most potent (IC50 = 2.18 mu M) inhibition against the enzyme tyrosinase which is more potent than the standard potent inhibitor L-mimosine IC50 = 3.68 mu M). This molecule can be the best candidate as a lead compound for further development of drug for the treatments of several skin disorders. (c) 2005 Elsevier Ltd. All rights reserved.