(Z)-4-(3-(cyclopentyloxy)-4-methoxybenzylidene)-2-phenyloxazol-5(4H)-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-4-(3-(cyclopentyloxy)-4-methoxybenzylidene)-2-phenyloxazol-5(4H)-one
• 英文别名: (4Z)-4-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-phenyl-1,3-oxazol-5-one
• 化学式: C₂₂H₂₁NO₄
• 分子量: 363.413
• InChiKey: KUCYQUHSBCUPCH-AQTBWJFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-4-(3-(cyclopentyloxy)-4-methoxybenzylidene)-2-phenyloxazol-5(4H)-one 在 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 ethyl 2-benzamido-3-(3-(cyclopentyloxy)-4-methoxyphenyl)propanoate
  参考文献：
  名称：

  用1-苯基-3,4-二氢异喹啉骨架发现新型磷酸二酯酶抑制剂4：基于结构的药物设计和片段鉴定。

  摘要：

  Currently, it is in urgent need to develop novel selective PDE4 inhibitors with novel structural scaffolds to overcome the adverse effects and improve the efficacy. Novel 1-phenyl-3,4-dihydroisoquinoline amide derivatives were developed as potential PDE4 inhibitors based on the structure-based drug design and fragment identification strategy. A SARs analysis was performed in substituents attached in the C-3 side chain phenyl ring, indicating that the attachment of methoxy group or halogen atom substitution at the ortho-position of the phenyl ring was helpful to enhance both inhibitory activity toward PDE4B and selectivity. Compound 15 with excellent selectivity, exhibited the most potent inhibition in vitro and in vivo, which is a promising lead for development of a new class of selective PDE4 inhibitors.

  DOI：

  10.1016/j.bmcl.2019.126720
• 作为产物：
  描述：

  马尿酸 、 3-环戊氧-4-甲氧基苯甲醛 在 sodium acetate 、 乙酸酐 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以67%的产率得到(Z)-4-(3-(cyclopentyloxy)-4-methoxybenzylidene)-2-phenyloxazol-5(4H)-one
  参考文献：
  名称：

  用1-苯基-3,4-二氢异喹啉骨架发现新型磷酸二酯酶抑制剂4：基于结构的药物设计和片段鉴定。

  摘要：

  Currently, it is in urgent need to develop novel selective PDE4 inhibitors with novel structural scaffolds to overcome the adverse effects and improve the efficacy. Novel 1-phenyl-3,4-dihydroisoquinoline amide derivatives were developed as potential PDE4 inhibitors based on the structure-based drug design and fragment identification strategy. A SARs analysis was performed in substituents attached in the C-3 side chain phenyl ring, indicating that the attachment of methoxy group or halogen atom substitution at the ortho-position of the phenyl ring was helpful to enhance both inhibitory activity toward PDE4B and selectivity. Compound 15 with excellent selectivity, exhibited the most potent inhibition in vitro and in vivo, which is a promising lead for development of a new class of selective PDE4 inhibitors.

  DOI：

  10.1016/j.bmcl.2019.126720