5-(2-hydroxy-4-methoxybenzoyl)-1-pentylpyridin-2(1H)-one | 1201816-80-9

• 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-pentylpyridin-2(1H)-one
• 英文别名: 5-(2-Hydroxy-4-methoxybenzoyl)-1-pentylpyridin-2-one
• CAS: 1201816-80-9
• 化学式: C₁₈H₂₁NO₄
• 分子量: 315.369
• InChiKey: ZSAKLXRABKJFTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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 、 1-氨基戊烷 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以88%的产率得到5-(2-hydroxy-4-methoxybenzoyl)-1-pentylpyridin-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

• 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。