icosyl 2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetate | 1217342-37-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: icosyl 2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetate
• 英文别名: icosyl 2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyacetate
• CAS: 1217342-37-4
• 化学式: C₃₇H₅₂O₆
• 分子量: 592.816
• InChiKey: GIBKNSMHWJEAQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  43
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(5-羟基-4-氧代-2-苯基-4H-色烯-7-基氧基)乙酸 、 1-二十醇 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以33%的产率得到icosyl 2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of chrysin long-chain derivatives as potential anticancer agents

  摘要：

  A series of long-chain derivatives of chrysin (compounds 3-22) were synthesized to evaluate for their antiproliferative activities against the human liver cancer cell line HT-29 and EGFR inhibitory activity. Among the compounds tested, compounds hexadecyl 2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy) acetate (10) and N-hexadecyl 2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy) acetamide (20) displayed potent EGFR inhibitory activity with IC50 values of 0.048 mu M and 0.035 mu M), comparable to the positive control erlotinib. Docking simulation of compounds 10 and 20 was carried out to illustrate the binding mode of the molecular into the EGFR active site, and the result suggested that compound 10 and 20 can bind the EGFR kinase well. Thus, compounds 10 and 20 with potent EGFR inhibitory activity would be potential anticancer agents. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.048

文献信息

• Design, synthesis and biological evaluation of chrysin long-chain derivatives as potential anticancer agents
  作者：Peng-Cheng Lv、Kai-Rui Wang、Qing-Shan Li、Jin Chen、Juan Sun、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2009.12.048

  日期：2010.2

  A series of long-chain derivatives of chrysin (compounds 3-22) were synthesized to evaluate for their antiproliferative activities against the human liver cancer cell line HT-29 and EGFR inhibitory activity. Among the compounds tested, compounds hexadecyl 2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy) acetate (10) and N-hexadecyl 2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy) acetamide (20) displayed potent EGFR inhibitory activity with IC50 values of 0.048 mu M and 0.035 mu M), comparable to the positive control erlotinib. Docking simulation of compounds 10 and 20 was carried out to illustrate the binding mode of the molecular into the EGFR active site, and the result suggested that compound 10 and 20 can bind the EGFR kinase well. Thus, compounds 10 and 20 with potent EGFR inhibitory activity would be potential anticancer agents. (C) 2009 Elsevier Ltd. All rights reserved.