5-((1H-indol-3-yl)methyl)-3-(3-(cyclopentyloxy)-4-methoxyphenyl)-1,2,4-oxadiazole | 1163715-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-((1H-indol-3-yl)methyl)-3-(3-(cyclopentyloxy)-4-methoxyphenyl)-1,2,4-oxadiazole
• 英文别名: 3-(3-cyclopentyloxy-4-methoxyphenyl)-5-(1H-indol-3-ylmethyl)-1,2,4-oxadiazole
• CAS: 1163715-98-7
• 化学式: C₂₃H₂₃N₃O₃
• 分子量: 389.454
• InChiKey: TWAXXSYSPWCYQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-羟基-4-甲氧基苯腈 在 盐酸羟胺 、 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 32.5h， 生成 5-((1H-indol-3-yl)methyl)-3-(3-(cyclopentyloxy)-4-methoxyphenyl)-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

文献信息

• Synthesis and anticancer activities of novel 3,5-disubstituted-1,2,4-oxadiazoles
  作者：Dalip Kumar、Gautam Patel、Emmanuel O. Johnson、Kavita Shah

  DOI：10.1016/j.bmcl.2009.03.158

  日期：2009.5

  A series of 3,5-disubstituted-1,2,4-oxadiazoles were synthesized and evaluated for their in vitro anti-proliferative activities against various cancer cell lines. Formation of 1,2,4-oxadiazole ring was accomplished by the reaction of amidoxime with carboxylic acids. The in vitro cytotoxic effects of 3,5-disubstituted-1,2,4-oxadiazoles have been demonstrated across a wide array of tumor cell types and

  合成了一系列3,5-二取代-1,2,4-恶二唑，并评估了它们对各种癌细胞的体外抗增殖活性。1,2,4-恶二唑环的形成是通过of胺肟与羧酸的反应完成的。已在多种肿瘤细胞类型中证明了3,5-二取代-1,2,4-恶二唑的体外细胞毒性作用，一些化合物对胰腺（3f，3h，3j和3k）和前列腺具有特异性（3n）癌细胞。在制备的3,5-二取代-1,2,4-恶二唑中，化合物3n的选择性最高（> 450倍），化合物3p 对前列腺癌细胞系具有最大的细胞毒性（10 nM）。