(E)-1-(2,4-difluorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(2,4-difluorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 化学式: C₁₆H₁₂F₂O₃
• 分子量: 290.266
• InChiKey: RTFYSTWYQDQPBZ-QHHAFSJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  异香兰素 、 2',4'-二氟苯乙酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以40.3%的产率得到(E)-1-(2,4-difluorophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of α-methyl-chalcone for anti-cervical cancer activity

  摘要：

  A series of 31 chalcones were synthesized and evaluated for anti-proliferative activity against the human cervical cancer cell lines (HeLa and SiHa). Compound 19, (E)-1-(2,4-dihydroxyphenyl)-3-(4-(dimethylamino)phenyl)-2-methylprop-2-en-1-one was found to be an effective anti-proliferative agent in HeLa and SiHa cells (IC50 = 0.035 mu M). Compound 19 increased the percentage of apoptosis in a dose-dependent manner, as measured by Annexin V-FITC (fluorescein isothiocyanate)/(propidium iodide) PI staining. Molecular modeling studies of compound 19 showed that the most potent structure was docked at the yeast 20 S proteasome binding site (Protein Data Bank code-3E47) and was stabilized in the cavity by various hydrophobic and hydrogen bonding interactions.

  DOI：

  10.1007/s00044-017-1891-0

文献信息

• Synthesis and biological evaluation of α-methyl-chalcone for anti-cervical cancer activity
  作者：Bing-zhao Ren、Mourboul Ablise、Xu-chao Yang、Bo-er Liao、Zheng Yang

  DOI：10.1007/s00044-017-1891-0

  日期：2017.9

  A series of 31 chalcones were synthesized and evaluated for anti-proliferative activity against the human cervical cancer cell lines (HeLa and SiHa). Compound 19, (E)-1-(2,4-dihydroxyphenyl)-3-(4-(dimethylamino)phenyl)-2-methylprop-2-en-1-one was found to be an effective anti-proliferative agent in HeLa and SiHa cells (IC50 = 0.035 mu M). Compound 19 increased the percentage of apoptosis in a dose-dependent manner, as measured by Annexin V-FITC (fluorescein isothiocyanate)/(propidium iodide) PI staining. Molecular modeling studies of compound 19 showed that the most potent structure was docked at the yeast 20 S proteasome binding site (Protein Data Bank code-3E47) and was stabilized in the cavity by various hydrophobic and hydrogen bonding interactions.