1-allyl-5-(2-hydroxy-4-methoxybenzoyl)-pyridin-2(1H)-one | 1201816-82-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-allyl-5-(2-hydroxy-4-methoxybenzoyl)-pyridin-2(1H)-one
• 英文别名: 1-allyl-5-(2-hydroxy-4-methoxybenzoyl)pyridin-2(1H)-one；5-(2-Hydroxy-4-methoxybenzoyl)-1-prop-2-enylpyridin-2-one
• CAS: 1201816-82-1
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: SODVIFBNZHRQDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-methyl 3-(7-methoxy-4-oxo-4H-chromen-3-yl)acrylate 、 丙烯胺 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以89%的产率得到1-allyl-5-(2-hydroxy-4-methoxybenzoyl)-pyridin-2(1H)-one
  参考文献：
  名称：

  Re-cyclization of 3-(E)-methyl 3-(4-oxo-4H-chromen-3-yl)acrylate with amines and their potential mechanism

  摘要：

  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.

  DOI：

  10.1016/j.tet.2013.08.032

文献信息

• Synthesis and anti-HBV activity of novel 5-substituted pyridin-2(1H)-one derivatives
  作者：Yi Kai Zhang、Zhi Liang Lv、Chun Juan Niu、Ke Li

  DOI：10.1016/j.cclet.2009.10.010

  日期：2010.3

  Abstract Four novel 5-substituted pyridine-2(1H)-one derivatives were designed and synthesized by using addition–elimination reactions. The structures of these novelly synthesized compounds were verified by 1 H NMR, ESI-MS and single crystal X-ray diffraction. Furthermore, all four compounds (most notably compound 7a ) were found to be highly efficient against hepatitis B virus (HBV) in cultured HepG2

  摘要设计了四种新的5-取代吡啶-2（1H）-one衍生物，并通过加成-消除反应合成。这些新颖合成的化合物的结构通过1 H NMR，ESI-MS和单晶X射线衍射验证。此外，发现所有四种化合物（最显着的化合物7a）在培养的HepG2 2.2.15细胞中对乙型肝炎病毒（HBV）都非常有效，这使其成为抗乙型肝炎潜在生物活性分子的有希望的候选药物。
• 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.