ethyl 5-[4-(4-chlorobenzyloxy)3-cyano-phenyl]isoxazole-3-carboxylate | 1198617-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 5-[4-(4-chlorobenzyloxy)3-cyano-phenyl]isoxazole-3-carboxylate
• 英文别名: Ethyl 5-[4-[(4-chlorophenyl)methoxy]-3-cyanophenyl]-1,2-oxazole-3-carboxylate
• CAS: 1198617-36-5
• 化学式: C₂₀H₁₅ClN₂O₄
• 分子量: 382.803
• InChiKey: CVJVIKUZSZTROK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (Z)-ethyl 4-[4-(4-chlorobenzyloxy)-3-cyanophenyl]-2-hydroxy-4-oxobut-2-enoate 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以76.7%的产率得到ethyl 5-[4-(4-chlorobenzyloxy)3-cyano-phenyl]isoxazole-3-carboxylate
  参考文献：
  名称：

  Synthesis of some 5-phenylisoxazole-3-carboxylic acid derivatives as potent xanthine oxidase inhibitors

  摘要：

  A number of 5-phenylisoxazole-3-carboxylic acid derivatives (5a-e, 11a-e) were synthesized and analyzed for their ability to inhibit xanthine oxidase. Most of the compounds exhibited potency levels in the micromolar/submicromolar range. The presence of a cyano group at the 3-position of phenyl moiety turned out to be the preferred substitution pattern, as its transformation into the nitro group determined a general reduction of the inhibitory potency. A molecular modeling study on compound 11a was performed to gain an insight into its binding mode with xanthine oxidase, and to provide the basis for further structure-guided design of new non-purine xanthine oxidase inhibitors related with 5-phenylisoxazole-3-carboxylic acid scaffold.

  DOI：

  10.1016/j.ejmech.2010.02.013

文献信息

• Synthesis of some 5-phenylisoxazole-3-carboxylic acid derivatives as potent xanthine oxidase inhibitors
  作者：Shaojie Wang、Jufang Yan、Jian Wang、Jiarun Chen、Tingjian Zhang、Yong Zhao、Mingxing Xue

  DOI：10.1016/j.ejmech.2010.02.013

  日期：2010.6

  A number of 5-phenylisoxazole-3-carboxylic acid derivatives (5a-e, 11a-e) were synthesized and analyzed for their ability to inhibit xanthine oxidase. Most of the compounds exhibited potency levels in the micromolar/submicromolar range. The presence of a cyano group at the 3-position of phenyl moiety turned out to be the preferred substitution pattern, as its transformation into the nitro group determined a general reduction of the inhibitory potency. A molecular modeling study on compound 11a was performed to gain an insight into its binding mode with xanthine oxidase, and to provide the basis for further structure-guided design of new non-purine xanthine oxidase inhibitors related with 5-phenylisoxazole-3-carboxylic acid scaffold.