N-{4-[(E)-2-(2,6-dihydroxy-5-nitropyrimidin-4-yl)ethenyl]phenyl}acetamide

• 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: N-{4-[(E)-2-(2,6-dihydroxy-5-nitropyrimidin-4-yl)ethenyl]phenyl}acetamide
• 英文别名: N-[4-[(E)-2-(5-nitro-2,4-dioxo-1H-pyrimidin-6-yl)ethenyl]phenyl]acetamide
• 化学式: C₁₄H₁₂N₄O₅
• 分子量: 316.273
• InChiKey: ZMUVFOJMPJAQCL-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-甲基尿嘧啶 在 哌啶 、 硫酸 、 硝酸 作用下， 以 正丁醇 为溶剂， 生成 N-{4-[(E)-2-(2,6-dihydroxy-5-nitropyrimidin-4-yl)ethenyl]phenyl}acetamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 5-Nitropyrimidine-2,4-dione Analogues as Inhibitors of Nitric Oxide and iNOS Activity

  摘要：

  Fifty two compounds based on 5‐nitropyrimidine‐2,4‐dione moiety have been synthesized and evaluated for their inhibitory potency on the production of nitric oxide. Among them, compound 36 inhibited the production of nitric oxide (IC50: 8.6 μm) on lipopolysaccharide‐induced RAW 264.7 cells and inducible nitric oxide synthase activity (IC50: 6.2 μm), as well as exerted no potential cytotoxicity (IC50 > 80.0 μm). Docking study confirmed that compound 36 was an inducible nitric oxide synthase inhibitor with perfect binding to the active site of inducible nitric oxide synthase. At a dose of 10 mg/kg, oral administration of 36 possessed protective properties in carrageenan‐induced paw edema of male ICR mice.

  DOI：

  10.1111/cbdd.12386

文献信息

• Synthesis and Biological Evaluation of 5-Nitropyrimidine-2,4-dione Analogues as Inhibitors of Nitric Oxide and iNOS Activity
  作者：Liang Ma、Linhong He、Lei Lei、Xiaolin Liang、Kai Lei、Ronghong Zhang、Zhuang Yang、Lijuan Chen

  DOI：10.1111/cbdd.12386

  日期：2015.3

  Fifty two compounds based on 5‐nitropyrimidine‐2,4‐dione moiety have been synthesized and evaluated for their inhibitory potency on the production of nitric oxide. Among them, compound 36 inhibited the production of nitric oxide (IC50: 8.6 μm) on lipopolysaccharide‐induced RAW 264.7 cells and inducible nitric oxide synthase activity (IC50: 6.2 μm), as well as exerted no potential cytotoxicity (IC50 > 80.0 μm). Docking study confirmed that compound 36 was an inducible nitric oxide synthase inhibitor with perfect binding to the active site of inducible nitric oxide synthase. At a dose of 10 mg/kg, oral administration of 36 possessed protective properties in carrageenan‐induced paw edema of male ICR mice.