(1E,4Z,6E)-1-(4-ethoxy-3-methoxyphenyl)-5-hydroxy-7-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (1E,4Z,6E)-1-(4-ethoxy-3-methoxyphenyl)-5-hydroxy-7-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
• 化学式: C₂₂H₂₂O₅
• 分子量: 366.414
• InChiKey: ZHLUWXVJLKAEGX-RLMHCWTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  curcumin 2 、 甲磺酸乙酯 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以50%的产率得到
  参考文献：
  名称：

  Influence of side-chain changes on histone deacetylase inhibitory and cytotoxicity activities of curcuminoid derivatives

  摘要：

  Using curcuminoids as lead compounds, fifty-nine curcuminoid derivatives with different side chains at the phenolic moiety were synthesized. All compounds were investigated for their histone deacetylase (HDAC) inhibitory activities. The potent pan-HDAC inhibitors were further tested against three human cancer cell lines including Hela, HCT116 and MCF-7 with MTT-based assay. The bisethylamide 4z and the mono-sec-butyl derivative 5j manifested good antiproliferative activities against HCT116 cancer cells with the IC50 values as 14.60 +/- 1.19 mu g/mL and 7.33 +/- 0.98 mu g/mL, respectively. Molecular docking study of both compounds with Class I HDACs revealed that the compounds might bind tightly to the binding pocket of HDAC2. These findings suggested that these compounds can be putative candidates for the development of anticancer drugs via inhibiting HDACs.

  DOI：

  10.1016/j.bmcl.2020.127171

文献信息

• Influence of side-chain changes on histone deacetylase inhibitory and cytotoxicity activities of curcuminoid derivatives
  作者：La-or Somsakeesit、Thanaset Senawong、Pakit Kumboonma、Somprasong Saenglee、Arunta Samankul、Gulsiri Senawong、Chavi Yenjai、Chanokbhorn Phaosiri

  DOI：10.1016/j.bmcl.2020.127171

  日期：2020.6

  Using curcuminoids as lead compounds, fifty-nine curcuminoid derivatives with different side chains at the phenolic moiety were synthesized. All compounds were investigated for their histone deacetylase (HDAC) inhibitory activities. The potent pan-HDAC inhibitors were further tested against three human cancer cell lines including Hela, HCT116 and MCF-7 with MTT-based assay. The bisethylamide 4z and the mono-sec-butyl derivative 5j manifested good antiproliferative activities against HCT116 cancer cells with the IC50 values as 14.60 +/- 1.19 mu g/mL and 7.33 +/- 0.98 mu g/mL, respectively. Molecular docking study of both compounds with Class I HDACs revealed that the compounds might bind tightly to the binding pocket of HDAC2. These findings suggested that these compounds can be putative candidates for the development of anticancer drugs via inhibiting HDACs.