(Z)-5-acetoxy-2-(4-diethylaminobenzylidene)benzofuran-3(2H)-one | 1261274-20-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-5-acetoxy-2-(4-diethylaminobenzylidene)benzofuran-3(2H)-one
• 英文别名: [(2Z)-2-[[4-(diethylamino)phenyl]methylidene]-3-oxo-1-benzofuran-5-yl] acetate
• CAS: 1261274-20-7
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: NAAMMDAESYYPMS-NDENLUEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-5-hydroxy-2-(4-diethylaminobenzylidene)benzofuran-3(2H)-one 、 乙酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到(Z)-5-acetoxy-2-(4-diethylaminobenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  Design, synthesis and discovery of 5-hydroxyaurone derivatives as growth inhibitors against HUVEC and some cancer cell lines

  摘要：

  A series of 4'-substituted 5-hydroxyaurone derivatives were synthesized and their inhibitory activities against the proliferation of endothelial cells and two cancer cell lines were studied. Some of these compounds functioned as potent inhibitors against the proliferation of endothelial cells and cancer cells but possessed much weaker cytotoxic activities against non-cancer cell line of CCC-HPF-1. It was demonstrated that two most active compounds 16 and 27 effectively inhibited in vitro endothelial cell motility and tube formation, which are basic properties of endothelial cells for angiogenesis. Moreover, 16 and 27 also showed significant activities against in vitro cancer cell invasion, indicating that they have potential to inhibit cancer metastasis. These composite results suggest that 4'-substituted 5-hydroxyaurone is indeed a candidate structural scaffold for anticancer agent targeting activated endothelial cells and fast-proliferating cancer cells. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.061

文献信息

• Design, synthesis and discovery of 5-hydroxyaurone derivatives as growth inhibitors against HUVEC and some cancer cell lines
  作者：Huimin Cheng、Lianwen Zhang、Yingxue Liu、Shaopeng Chen、Hao Cheng、Xin Lu、Zhuxia Zheng、Guo-Chun Zhou

  DOI：10.1016/j.ejmech.2010.09.061

  日期：2010.12

  A series of 4'-substituted 5-hydroxyaurone derivatives were synthesized and their inhibitory activities against the proliferation of endothelial cells and two cancer cell lines were studied. Some of these compounds functioned as potent inhibitors against the proliferation of endothelial cells and cancer cells but possessed much weaker cytotoxic activities against non-cancer cell line of CCC-HPF-1. It was demonstrated that two most active compounds 16 and 27 effectively inhibited in vitro endothelial cell motility and tube formation, which are basic properties of endothelial cells for angiogenesis. Moreover, 16 and 27 also showed significant activities against in vitro cancer cell invasion, indicating that they have potential to inhibit cancer metastasis. These composite results suggest that 4'-substituted 5-hydroxyaurone is indeed a candidate structural scaffold for anticancer agent targeting activated endothelial cells and fast-proliferating cancer cells. (C) 2010 Elsevier Masson SAS. All rights reserved.