1-(2-hydroxy-4-methoxyphenyl)-3-(piperidin-1-yl)prop-2-en-1-one | 1388223-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(2-hydroxy-4-methoxyphenyl)-3-(piperidin-1-yl)prop-2-en-1-one
• CAS: 1388223-86-6
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: DTBWLBYKIAGJCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  435.8±45.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-4-methoxyphenyl)-3-(piperidin-1-yl)prop-2-en-1-one 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 5-(2-hydroxy-4-methoxybenzoyl)-1-o-tolylphenylpyridin-2(1H)-one
  参考文献：
  名称：

  Design and synthesis of novel 2′-hydroxy group substituted 2-pyridone derivatives as anticancer agents

  摘要：

  We have synthesized a series of novel 2-pyridone derivatives with 1,2,3-triazole and evaluated their antitumor activities in vitro. The bioassays showed that the majority of the resultant compounds exerted inhibitory effects on six human cancer cell lines to various extents. In particular, compound 10k showed the best anti-tumor activities (IC50 values of A549, HeLa and SW480 cancer cell lines were 0.86 +/- 0.17 mu M, 0.54 +/- 0.23 mu M and 0.21 +/- 0.13 mu M, respectively). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.046
• 作为产物：
  描述：

  3-hydroxy-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one 在 盐酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 1-(2-hydroxy-4-methoxyphenyl)-3-(piperidin-1-yl)prop-2-en-1-one
  参考文献：
  名称：

  Anti-hepatitis B virus and anti-cancer activities of novel isoflavone analogs

  摘要：

  We have synthesized a series of novel isoflavone analogs and evaluated their anti-HBV and anti-cancer activities in vitro. The bioassays showed that the majority of the resultant compounds exerted inhibitory effects on HBsAg and HBeAg levels, HBV DNA replication, as well as the growth of four human cancer cell lines to various extents, which supported the rationale of the design. In particular, compound 8f showed the highest activity against HBV infection and HBV-related liver cancer. Compound 71 (IC50 = 0.47 mu M) also exerted remarkable inhibitory effect on the growth lung cancer cell line A-549. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.017

文献信息

• Efficient Heck cross-coupling of 3-iodo-benzopyrones with olefins under microwave irradiation without phosphine
  作者：Yikai Zhang、Zhiliang Lv、Hanyu Zhong、Mingfeng Zhang、Tao Zhang、Wannian Zhang、Ke Li

  DOI：10.1016/j.tet.2012.09.017

  日期：2012.11

  different terminal olefins with various 3-iodo-benzopyrones including sterically hindered, electron-rich, electron-neutral, and electron-deficient is developed. It proceeded faster and generally gave good to excellent yields under microwave irradiation, phosphine-free, and air condition. The reaction could render this method particularly attractive for the efficient preparation of biologically and

  研究了不同末端烯烃与各种3-碘-苯并吡喃酮的高效，有效的微波辅助Heck交叉偶联，包括空间位阻，富电子，电子中性和电子缺陷的3-碘-苯并吡喃酮。在微波辐射，无磷化氢和空气条件下，它进行得更快，并且通常具有优异的收率。该反应可使该方法对于有效制备生物学和医学上感兴趣的分子特别有吸引力。
• 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.