2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromene-4-selenone

• 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: 2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromene-4-selenone
• 英文别名: 2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,7-dimethoxychromene-4-selone；2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxychromene-4-selone
• 化学式: C₁₉H₁₈O₆Se
• 分子量: 421.308
• InChiKey: UJELBPZPKPZGEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  槲皮素 在 Woollins 试剂 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 0.08h， 生成 2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromene-4-selenone
  参考文献：
  名称：

  Selenium-Containing Chrysin and Quercetin Derivatives: Attractive Scaffolds for Cancer Therapy

  摘要：

  Selenium-containing chrysin (SeChry) and 3,7,3',4'-tetramethylquercetin (SePQue) derivatives were synthesized by a microwave-based methodology. In addition to their improvement in terms of DPPH Scavenging and potential GPx-like activities, when tested in a panel of cancer cell lines both selenium-derivatives revealed consistently to be more cytoxic when compared with their oxo and thioanalogues, evidencing the key role of selenocabonyl Moiety for these activities In particular, SeChry elicited a noteworthy cytotoxic activity with mean IC50 values 18- and 3-fold lower than those observed for chrysin and cisplatin, respectively. Additionally, these seleno-derivatives evidenced an ability to overcome cisplatin and multidrug resistance. Notably, a differential behavior toward malignant and nonmalignant cells Was observed for SeChry and SePQue, exhibiting higher selectivity indexes when compared with the chalcogen-derivatives and cisplatin. Our preliminary investigation on the mechanism of cytotoxicity of SeChry and SePQue in MCF-7 human mammary cancer cells demonstrated their capacity to efficiently suppress the clonal expansion along with their ability to hamper TrxR activity leading to apoptotic cell death.

  DOI：

  10.1021/acs.jmedchem.5b00230

文献信息

• Selenium-Containing Chrysin and Quercetin Derivatives: Attractive Scaffolds for Cancer Therapy
  作者：Inês L. Martins、Catarina Charneira、Valentina Gandin、João L. Ferreira da Silva、Gonçalo C. Justino、João P. Telo、Abel J. S. C. Vieira、Cristina Marzano、Alexandra M. M. Antunes

  DOI：10.1021/acs.jmedchem.5b00230

  日期：2015.5.28

  Selenium-containing chrysin (SeChry) and 3,7,3',4'-tetramethylquercetin (SePQue) derivatives were synthesized by a microwave-based methodology. In addition to their improvement in terms of DPPH Scavenging and potential GPx-like activities, when tested in a panel of cancer cell lines both selenium-derivatives revealed consistently to be more cytoxic when compared with their oxo and thioanalogues, evidencing the key role of selenocabonyl Moiety for these activities In particular, SeChry elicited a noteworthy cytotoxic activity with mean IC50 values 18- and 3-fold lower than those observed for chrysin and cisplatin, respectively. Additionally, these seleno-derivatives evidenced an ability to overcome cisplatin and multidrug resistance. Notably, a differential behavior toward malignant and nonmalignant cells Was observed for SeChry and SePQue, exhibiting higher selectivity indexes when compared with the chalcogen-derivatives and cisplatin. Our preliminary investigation on the mechanism of cytotoxicity of SeChry and SePQue in MCF-7 human mammary cancer cells demonstrated their capacity to efficiently suppress the clonal expansion along with their ability to hamper TrxR activity leading to apoptotic cell death.