[5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl] 2-methylbenzoate | 1416850-02-6

• 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: [5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl] 2-methylbenzoate
• 英文别名: [5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl] 2-methylbenzoate
• CAS: 1416850-02-6
• 化学式: C₂₃H₁₈O₆
• 分子量: 390.392
• InChiKey: PFHCUKXSSUWZIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  柚皮素 、 邻甲基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以66.3%的产率得到[5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl] 2-methylbenzoate
  参考文献：
  名称：

  Design, synthesis and inhibitory activities of naringenin derivatives on human colon cancer cells

  摘要：

  Based on the previous result, several naringenin derivatives modified at position 7 with bulky substituents were designed and synthesized, and their inhibitory effects on HCT116 human colon cancer cells were tested using a clonogenic assay. The half maximal inhibitory concentrations (IC50) of five naringenin derivatives ranged between 1.20 mu M and 20.01 mu M which are much better than naringenin used as a control. In addition, new structural modification at C-4 of flavanone results in improving both the anti-cancer effect and anti-oxidative effect. In vitro cyclin dependent kinase 2 (CDK2) binding assay was carried out based on the previous results. To elucidate the possible interaction between naringenin derivatives and CDK2, in silico docking study was performed. This result demonstrates the rationale for the different inhibitory activities of the naringenin derivatives. These findings could be used for designing cancer therapeutic or preventive flavanone-derived agents. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.130

文献信息

• Design, synthesis and inhibitory activities of naringenin derivatives on human colon cancer cells
  作者：Hyuk Yoon、Tae Woo Kim、Soon Young Shin、Mi Joo Park、Yeonjoong Yong、Dong Woon Kim、Tasneem Islam、Young Han Lee、Kang-Yeoun Jung、Yoongho Lim

  DOI：10.1016/j.bmcl.2012.10.130

  日期：2013.1

  Based on the previous result, several naringenin derivatives modified at position 7 with bulky substituents were designed and synthesized, and their inhibitory effects on HCT116 human colon cancer cells were tested using a clonogenic assay. The half maximal inhibitory concentrations (IC50) of five naringenin derivatives ranged between 1.20 mu M and 20.01 mu M which are much better than naringenin used as a control. In addition, new structural modification at C-4 of flavanone results in improving both the anti-cancer effect and anti-oxidative effect. In vitro cyclin dependent kinase 2 (CDK2) binding assay was carried out based on the previous results. To elucidate the possible interaction between naringenin derivatives and CDK2, in silico docking study was performed. This result demonstrates the rationale for the different inhibitory activities of the naringenin derivatives. These findings could be used for designing cancer therapeutic or preventive flavanone-derived agents. (c) 2012 Elsevier Ltd. All rights reserved.