3,3',4',7-tetramethoxy-5-hydroxyflavothione | 1203579-92-3

• 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: 3,3',4',7-tetramethoxy-5-hydroxyflavothione
• 英文别名: 2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,7-dimethoxychromene-4-thione；2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxychromene-4-thione
• CAS: 1203579-92-3
• 化学式: C₁₉H₁₈O₆S
• 分子量: 374.414
• InChiKey: QSSITKBBFBLDNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  98.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,3',4',7-tetramethoxy-5-hydroxyflavothione 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以86%的产率得到2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromene-4-thione
  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
• 作为产物：
  描述：

  槲皮素 在 tetraphosphorus decasulfide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 72.0h， 生成 3,3',4',7-tetramethoxy-5-hydroxyflavothione
  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

• NMR of a series of novel hydroxyflavothiones
  作者：Tuyen Kim Pham Nguyen、Kim Phi Phung Nguyen、Fadhil S. Kamounah、Wei Zhang、Poul Erik Hansen

  DOI：10.1002/mrc.2510

  日期：2009.12

  Alkylated hydroxyflavothiones, namely flavothione, 5-hydroxyflavothione, 5,7-dihydroxyflavothione (chrysinthione), 7-dodecyloxy-5-hydroxyflavothione, 7-butyloxy-5-hydroxyflavothione, 2',3,4',7-tetramethoxy-5-hydroxyflavothione, 3,3',4',7-tetramethoxy-5-hydroxyflavothione, 7-butyloxy-4',5-dihydroxyflavothione and 7-butyloxy-4',5-hydroxyflavanonethione have been synthesized from the corresponding hydroxyflavones

  烷基化的羟基黄酮硫酮，即黄酮硫酮，5-羟基黄酮硫酮，5,7-二羟基黄酮硫酮（chrysinthione），7-十二烷氧基-5-羟基黄酮硫酮，7-丁氧基-5-羟基黄酮硫酮，2'，3,4'，7-四甲氧基-5-羟基黄酮硫酮在两个步骤中，由烷基化的羟基黄酮合成了3,3'，4'，7-四甲氧基-5-羟基黄酮硫酮，7-丁氧基-4'，5-二羟基黄酮硫酮和7-丁氧基-4'，5-羟基黄酮硫酮溴代烷烃或硫酸二甲酯对非氢键合的羟基进行分析，然后在微波辐射和无溶剂条件下使用Lawesson试剂将羰基转化为硫酮。在用Lawesson'处理的过程中，部分烷基化的黄烷酮7-丁氧基-4'，5-二羟基黄烷酮被氧化 除了目标产物丁氧基-4'，5-羟基黄烷硫酮以外，还可以得到第二种产物7-丁氧基-4'，5-二羟基黄烷硫酮。氘同位素对13C化学位移的影响已在羟基黄酮，异黄酮，黄烷酮和硫代类似物中进行了测量。正式的四键氘同位素对13C化学位移的影响，nDeltaC
• 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.