5,7-dimethoxy-2-[2-(4-nitrophenyl)vinyl]chromen-4-one | 1382529-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5,7-dimethoxy-2-[2-(4-nitrophenyl)vinyl]chromen-4-one
• 英文别名: 5,7-Dimethoxy-2-[2-(4-nitrophenyl)ethenyl]chromen-4-one
• CAS: 1382529-03-4
• 化学式: C₁₉H₁₅NO₆
• 分子量: 353.331
• InChiKey: BIMGXYVXRXCSMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5,7-二甲氧基-2-甲基-4H-苯并吡喃-4-酮 、 对硝基苯甲醛 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 5,7-dimethoxy-2-[2-(4-nitrophenyl)vinyl]chromen-4-one
  参考文献：
  名称：

  Synthesis of 2-styrylchromones as a novel class of antiproliferative agents targeting carcinoma cells

  摘要：

  A series of 2-styrylchromone analogs were synthesized and examined for their antiproliferative effects on a panel of carcinoma cells. Among the tested agents, only 4m exhibited a moderate activity with an IC(50) value of 28.9 mu M against PC-3 cells which indicates the selectivity of PC-3 cells in response to 2-styrylchromones. In addition, 4q demonstrated the most antiproliferative effect with an IC50 value of 4.9 mu M against HeLa cells. Flow cytometric analysis and DAPI staining revealed that HeLa cells exposed to 4q as low as 5 mu M induced cell death through sub-G1 arrest and DNA fragmentation. Furthermore, CoMFA analysis of tested 2-styrylchromones resulted in a q(2) of 0.459 to generate a 3D-QSAR model on BT483 cell line. Together, these results suggest a potential structural optimization and pharmacological study of 2-styrylchromones. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.034