5,7-Dihydroxyflavothione

• 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: 5,7-Dihydroxyflavothione
• 英文别名: 5,7-Dihydroxy-2-phenylchromene-4-thione；5,7-dihydroxy-2-phenylchromene-4-thione
• 化学式: C₁₅H₁₀O₃S
• 分子量: 270.309
• InChiKey: UKDLZIDPRIDTDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  白杨素 在 劳森试剂 作用下， 以8%的产率得到5,7-Dihydroxyflavothione
  参考文献：
  名称：

  一系列新型羟基黄酮的NMR。

  摘要：

  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

  DOI：

  10.1002/mrc.2510

文献信息

• Novel synthesised flavone derivatives provide significant insight into the structural features required for enhanced anti-proliferative activity
  作者：Divyashree Ravishankar、Kimberly A. Watson、Francesca Greco、Helen M. I. Osborn

  DOI：10.1039/c6ra11041j

  日期：——

  = 1.81 μM)). Overall, 15f and 16f exhibited 7–46 fold greater anti-proliferative potency than the natural flavone chrysin (2d). A systematic structure–activity relationship study against the breast cancer cell lines highlighted that free hydroxyl groups and the B-ring phenyl groups were essential for enhanced anti-proliferative activities. Substitution of the 4-CO functionality with a 4-CS functionality

  随着许多癌症显示出对当前化学疗法的抗性，寻找新型抗癌药引起了极大的关注。天然类黄酮已被确认为此类计划的有用线索。然而，由于通常缺乏对最佳活性的结构要求的深入了解，因此在实现类黄酮作为抗增殖剂的全部潜力之前，需要进行进一步的研究。本文构建了一个包含76个甲氧基和羟基黄酮及其4-硫代类似物的宽泛文库，并建立了它们与乳腺癌细胞系MCF-7（ER + ve），MCF-7 /的抗增殖活性的结构-活性关系。探测了DX（ER + ve，抗蒽环类）和MDA-MB-231（ER -ve）。在该库中，有42种化合物是新颖的，所有化合物的收率都很高，纯度95％。最有前途的先导化合物，特别是新型羟基4-硫代黄酮美国国家癌症研究所（NCI）进一步评估了15f和16f对多种癌细胞系的抗增殖活性，并显示出显着的生长抑制特征（例如化合物15f：MCF-7（GI 50 = 0.18μM），T-47D（GI 50 = 0.03μM）和MDA-MB-468（GI
• 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
• Photophysical Properties of Hydroxy-Substituted Flavothiones
  作者：Fausto Elisei、João C. Lima、Fausto Ortica、Gian G. Aloisi、Manuela Costa、Emília Leitão、Isabel Abreu、António Dias、Vasco Bonifácio、Jorge Medeiros、António L. Maçanita、Ralph S. Becker

  DOI：10.1021/jp000084y

  日期：2000.6.1

  Flavothione and a number of synthesized hydroxy- (mono- and di-) substituted flavothiones have been thoroughly examined, particularly regarding their absorption, emission, photophysical (triplet yields and lifetimes), and oxygen-photosensitizing characteristics. These were all studied as a function of the nature of the solvent (four), which was particularly critical in terms of aiding in determining the energy and configurational nature of the lowest triplet state as well as the mechanism of intersystem crossing. Theoretical calculations were also performed. Both the location and number of hydroxyl groups have a substantial impact on the nature of the lowest excited triplet state as well as on the relative location of the two lowest excited singlet and triplet states. These in turn affect the magnitude and even the existence of triplet-state occupation as well as the ability to sensitize oxygen (to singlet oxygen). Three groups of compounds exist as characterized by the configurational nature of the triplet and the mechanism of intersystem crossing, or the essential absence of intersystem crossing altogether. The quantum yield of singlet oxygen formation is high for one group where the T(pi, pi*) state is lowest and generally high in another group where the T(n, pi*) state is lowest, except in ethanol where competitive H-atom abstraction occurs. The potential of all hydroxy compounds as photosensitizers is evaluated.
• 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.