5-(2-hydroxy-4-methoxybenzoyl)-1-(4-nitrophenyl)pyridin-2(1H)-one | 1201816-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(2-hydroxy-4-methoxybenzoyl)-1-(4-nitrophenyl)pyridin-2(1H)-one
• 英文别名: 5-(2-Hydroxy-4-methoxybenzoyl)-1-(4-nitrophenyl)pyridin-2-one
• CAS: 1201816-75-2
• 化学式: C₁₉H₁₄N₂O₆
• 分子量: 366.33
• InChiKey: RDUANONEZHWIJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (E)-methyl 3-(7-methoxy-4-oxo-4H-chromen-3-yl)acrylate 、 4-硝基苯胺 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以35%的产率得到5-(2-hydroxy-4-methoxybenzoyl)-1-(4-nitrophenyl)pyridin-2(1H)-one
  参考文献：
  名称：

  Design, Synthesis, and Antihepatitis B Virus Activities of Novel 2-Pyridone Derivatives

  摘要：

  A series of novel 2-pyridone derivatives were synthesized and evaluated for their antihepatitis B virus (HBV) activity and cytotoxicity in vitro. Moderate to good activity against HBV DNA replication was observed in these 2-pyridone analogues. The most active compounds were 5d and 61, with good inhibitory activity against HBV DNA replication (IC50 = 0.206 and 0.12 mu M, respectively) and remarkable high selectivity (selectivity indexes of >532 and 467, respectively). A pharmacophore model of the synthesized compounds was proposed by the GASP program. The pharmacophore model consists of three hydrophobic points, four HBA points, and one HBD point. The 2-pyridone derivatives represent a novel class of HBV inhibitors, which are worth further optimization.

  DOI：

  10.1021/jm901237x

文献信息

• Design, Synthesis, and Antihepatitis B Virus Activities of Novel 2-Pyridone Derivatives
  作者：Zhiliang Lv、Chunquan Sheng、Tiantian Wang、Yikai Zhang、Jia Liu、Jilu Feng、Hailing Sun、Hanyu Zhong、Chunjuan Niu、Ke Li

  DOI：10.1021/jm901237x

  日期：2010.1.28

  A series of novel 2-pyridone derivatives were synthesized and evaluated for their antihepatitis B virus (HBV) activity and cytotoxicity in vitro. Moderate to good activity against HBV DNA replication was observed in these 2-pyridone analogues. The most active compounds were 5d and 61, with good inhibitory activity against HBV DNA replication (IC50 = 0.206 and 0.12 mu M, respectively) and remarkable high selectivity (selectivity indexes of >532 and 467, respectively). A pharmacophore model of the synthesized compounds was proposed by the GASP program. The pharmacophore model consists of three hydrophobic points, four HBA points, and one HBD point. The 2-pyridone derivatives represent a novel class of HBV inhibitors, which are worth further optimization.
• Re-cyclization of 3-(E)-methyl 3-(4-oxo-4H-chromen-3-yl)acrylate with amines and their potential mechanism
  作者：Yikai Zhang、Zhiliang Lv、Mingfeng Zhang、Ke Li

  DOI：10.1016/j.tet.2013.08.032

  日期：2013.10

  The synthesis of 2-pyridone derivatives from different substituted amines and various 3-(E)-methyl 3-(4-oxo-4H-chromen-3-yl)acrylate derivatives was proposed and described. The optimized reaction conditions and the generality of the reaction were investigated, respectively. Moreover, less side products could be formed than the traditional method. Finally, based on the fact that (E)-methyl 2-(7-methoxy-4-oxo-3-((phenylamino)methylene)chroman-2-yl)acetate was separated and determined via X-ray single crystal diffraction, we could propose an interesting and reasonable reaction mechanism for the first time. The reaction could render this method particularly attractive for the efficient preparation of biologically and medicinally interesting molecules. (c) 2013 Elsevier Ltd. All rights reserved.