3-(3-cyclopentyloxy-4-methoxyphenyl)-5-(3,4-dimethoxystyryl)-1,2,4-oxadiazole | 1374349-28-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(3-cyclopentyloxy-4-methoxyphenyl)-5-(3,4-dimethoxystyryl)-1,2,4-oxadiazole
• 英文别名: 3-(3-cyclopentyloxy-4-methoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethenyl]-1,2,4-oxadiazole
• CAS: 1374349-28-6
• 化学式: C₂₄H₂₆N₂O₅
• 分子量: 422.481
• InChiKey: VMFVFCRBYAMZQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.84
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  异香兰素 在 甲酸 、 盐酸羟胺 、 sodium formate 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.5h， 生成 3-(3-cyclopentyloxy-4-methoxyphenyl)-5-(3,4-dimethoxystyryl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Design and Synthesis of 3,5-Disubstituted-1,2,4-Oxadiazoles as Potent Inhibitors of Phosphodiesterase4B2

  摘要：

  A series of 3,5‐disubstituted‐1,2,4‐oxadiazoles has been prepared and evaluated for phosphodiesterase inhibition (PDE4B2). Among the prepared 3,5‐disubstituted‐1,2,4‐oxadiazoles, compound 9a is the most potent inhibitor (PDE4B2 IC50 = 5.28 μm). Structure–activity relationship studies of 3,5‐disubstituted‐1,2,4‐oxadiazoles revealed that substituents 3‐cyclopentyloxy‐4‐methoxyphenyl group at 3‐position and cyclic ring bearing heteroatoms at 5‐position are important for activity. Molecular modeling study of the 3,5‐disubstituted‐1,2,4‐oxadiazoles with PDE4B has shown similar interactions of 3‐cyclopentyloxy‐4‐methoxyphenyl group; however, heteroatom ring is slightly deviating when compared to Piclamilast. 3‐(3‐Cyclopentyloxy‐4‐methoxyphenyl)‐5‐(piperidin‐4‐yl)‐1,2,4‐oxadiazole (9a) exhibited good analgesic and antiinflammatory activities in formalin‐induced pain in mice and carrageenan‐induced paw edema model in rat.

  DOI：

  10.1111/j.1747-0285.2011.01304.x