5-hydroxy-4-oxo-2-phenylchroman-7-yl benzoate

• 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-4-oxo-2-phenylchroman-7-yl benzoate
• 英文别名: Pinocembrin 7-O-benzoate；(5-hydroxy-4-oxo-2-phenyl-2,3-dihydrochromen-7-yl) benzoate
• 化学式: C₂₂H₁₆O₅
• 分子量: 360.366
• InChiKey: FQYXLHNQZRKBPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲酰氯 、 乔松素 在 三乙胺 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以83%的产率得到5-hydroxy-4-oxo-2-phenylchroman-7-yl benzoate
  参考文献：
  名称：

  In vitro anti-proliferative and anti-bacterial properties of new C7 benzoate derivatives of pinocembrin

  摘要：

  In the present work, the in vitro anti-proliferative and anti-bacterial activities of three semi-synthetic benzoate pinocembrin derivatives, isolated from the aerial parts of Glycyrrhiza glabra L., were investigated. As occurs in most natural compounds, the bioavailability of pinocembrin is very poor, therefore it should be improved by chemical strategies aimed to prolong its shelf life and, consequently, its activity. On this basis, three benzoate derivatives of pinocembrin (a1-a3) were synthesised and assayed in order to ascertain their biological value. Among them, compound a1 showed the highest anti-proliferative activity on a wide panel of cancer cell lines, as well as low toxic effects on non-malignant breast cells. The calculated IC50 values in HeLa and SKBR3 cells were 8.5 and 12.7 mu M, respectively. Briefly, a1 treatment increased ROS levels, induced mitochondrial membrane damage leading to necrotic death of HeLa cells. Moreover, a1 displayed a promising anti-bacterial activity.[GRAPHICS].

  DOI：

  10.1080/14786419.2019.1641805

文献信息

• In vitro anti-proliferative and anti-bacterial properties of new C7 benzoate derivatives of pinocembrin
  作者：Anna R. Cappello、Francesca Aiello、Nicoletta Polerà、Biagio Armentano、Ivan Casaburi、Maria Luisa Di Gioia、Monica R. Loizzo、Vincenza Dolce、Vincenzo Pezzi、Rosa Tundis

  DOI：10.1080/14786419.2019.1641805

  日期：2021.6.3

  In the present work, the in vitro anti-proliferative and anti-bacterial activities of three semi-synthetic benzoate pinocembrin derivatives, isolated from the aerial parts of Glycyrrhiza glabra L., were investigated. As occurs in most natural compounds, the bioavailability of pinocembrin is very poor, therefore it should be improved by chemical strategies aimed to prolong its shelf life and, consequently, its activity. On this basis, three benzoate derivatives of pinocembrin (a1-a3) were synthesised and assayed in order to ascertain their biological value. Among them, compound a1 showed the highest anti-proliferative activity on a wide panel of cancer cell lines, as well as low toxic effects on non-malignant breast cells. The calculated IC50 values in HeLa and SKBR3 cells were 8.5 and 12.7 mu M, respectively. Briefly, a1 treatment increased ROS levels, induced mitochondrial membrane damage leading to necrotic death of HeLa cells. Moreover, a1 displayed a promising anti-bacterial activity.[GRAPHICS].