2',3,4-三羟基查耳酮 | 6272-43-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 2',3,4-三羟基查耳酮
• 英文名称: 2',3'',4''-trihydroxychalcone
• 英文别名: NCI37433；NSC37433；3-(3,4-Dihydroxyphenyl)-1-(2-hydroxyphenyl)-2-propen-1-one；3-(3,4-dihydroxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 6272-43-1
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: PSYVAIWGYVDYHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2',3,4-三羟基查耳酮 在 双氧水 、 二乙胺 作用下， 以 四氢呋喃 为溶剂， 以42%的产率得到3-hydroxy-2-(3′,4′-dihydroxyphenyl)chroman-4-one
  参考文献：
  名称：

  二氢黄酮醇衍生物的设计，合成及抗炎活性

  摘要：

  设计并合成了三十种二氢黄酮醇衍生物（D1 - D30），同时在光谱分析的基础上对合成的化合物进行了表征。它们对脂多糖（LPS）刺激的鼠RAW 264.7巨噬细胞中促炎性诱导白介素1β（IL-1β），白介素6（IL-6）和肿瘤坏死因子-α（TNF-α）的抑制活性为评估并显示出各种效率。化合物D1 - D30在20μM的浓度下对RAW 264.7细胞无毒作用；其中，化合物D9，D13和D19通过降低IL-1β，IL-6和TNF-α表现出最佳的抗炎活性。此外，初步讨论了它们的结构-活性关系。

  DOI：

  10.1007/s00044-017-2054-z
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 3,4-二羟基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2',3,4-三羟基查耳酮
  参考文献：
  名称：

  二氢黄酮醇衍生物的设计，合成及抗炎活性

  摘要：

  设计并合成了三十种二氢黄酮醇衍生物（D1 - D30），同时在光谱分析的基础上对合成的化合物进行了表征。它们对脂多糖（LPS）刺激的鼠RAW 264.7巨噬细胞中促炎性诱导白介素1β（IL-1β），白介素6（IL-6）和肿瘤坏死因子-α（TNF-α）的抑制活性为评估并显示出各种效率。化合物D1 - D30在20μM的浓度下对RAW 264.7细胞无毒作用；其中，化合物D9，D13和D19通过降低IL-1β，IL-6和TNF-α表现出最佳的抗炎活性。此外，初步讨论了它们的结构-活性关系。

  DOI：

  10.1007/s00044-017-2054-z

文献信息

• Fluorinated 2′-hydroxychalcones as garcinol analogs with enhanced antioxidant and anticancer activities
  作者：Subhash Padhye、Aamir Ahmad、Nikhil Oswal、Prasad Dandawate、Rukhsana A. Rub、Jyoti Deshpande、K. Venkateswara Swamy、Fazlul H. Sarkar

  DOI：10.1016/j.bmcl.2010.07.128

  日期：2010.10

  these limitations in case of 2′-hydroxychalcones through bioisosteric substitution of fluoro groups in place of phenolic hydroxyls. The fluorinated chalcones were found to be more potent antioxidant and anti-proliferative compounds than their hydroxyl counterparts indicating the influence of metabolically stable C–F bonds towards bioavailability. The difluoro derivatives were found to be most effective

  查耳酮参与类黄酮的合成，其本身已知具有多种药理特性。但是，与其他结构相似的植物化学物质（如藤黄酚和姜黄素）相比，查耳酮的治疗用途受到限制，因为它们的生物利用度较低，并且可以从生物系统中快速清除新陈代谢。在目前的工作中，我们试图通过氟的生物等位取代酚羟基来克服2'-羟基查耳酮的这些局限性。发现氟化查耳酮比羟基查耳酮更有效的抗氧化剂和抗增殖化合物，表明代谢稳定的CF键对生物利用度的影响。
• Aspergillus niger catalyzes the synthesis of flavonoids from chalcones
  作者：Julio Alarcón、Joel Alderete、Carlos Escobar、Ramiro Araya、Carlos L. Cespedes

  DOI：10.3109/10242422.2013.813489

  日期：2013.8

  Flavonoids, which have many biological activities and have been widely used in nature, can be artificially synthesized. However, regioselective cyclization of chalcones is difficult by chemical methods. In this study, we demonstrated that Aspergillus niger is capable of cyclizing chalcones to flavanones, affording a mimic of plant biosynthetic processes. Chalcones 1-6 were biotransformated to the modified chalcones 8-14 and to the flavanones 15-27. The biotransformation showed that enzymatic cyclization and demethylation occurred during the first days of biotransformation; in contrast, hydroxylation is a later process. With a longer culturing time, it is possible to obtain more hydroxylated flavanones with excellent yields.
• Design and synthesis of 3,5-diaryl-4,5-dihydro-1H-pyrazoles as new tyrosinase inhibitors
  作者：Zhixuan Zhou、Jiaru Zhuo、Sujun Yan、Lin Ma

  DOI：10.1016/j.bmc.2012.12.054

  日期：2013.4

  In this study, twenty 3,5-diaryl-4,5-dihydro-1H-pyrazole derivatives with hydroxyl(s) (1a-1p, 2a-2d) were synthesized and their inhibitory activity on mushroom tyrosinase was examined. The results showed that among these compounds, 1-(5-(3,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone 1d was found to be the most potent tyrosinase inhibitor with IC50 value of 0.301 mu M. Kinetic study revealed that these compounds were competitive inhibitors of tyrosinase and their structure-activity relationships were investigated in this article. (C) 2013 Published by Elsevier Ltd.
• Natural product-based design, synthesis and biological evaluation of 2′,3,4,4′-tetrahydrochalcone analogues as antivitiligo agents
  作者：Hui Zhong、Jia Zhou、Xiao-Hong An、Ying-Rong Hua、Yi-Fan Lai、Rui Zhang、Owais Ahmad、Ye Zhang、Jing Shang

  DOI：10.1016/j.bioorg.2019.03.054

  日期：2019.6

  A bioactive component, 2',3,4,4'-tetrahydrochalcone (RY3-a) was first isolated from Vernohia anthelmintica (L.) willd seeds, and a set of its analogs, RY3-a-1-RY3-a-15 and RY3-c were designed and synthesized. Biological activity assays showed that RY3-c exhibited better melanogenesis and antioxidant activity and lower toxicity in comparison with RY3-a and butin. Further study tests showed that RY3-c exhibited better melanogenesis activity compared with the positive control 8-methoxypsoralan (8-MOP) in a vitiligo mouse model, suggesting that RY3-c is a good candidate antivitiligo agent. Mechanistic studies showed that RY3-c could repair cell damage induced by excessive oxidative stress and may exert melanin synthesis activity in the mouse melanoma B16F10 cell line by activating the mitogen-activated protein kinase (MAPK) pathway and the upregulation of c-kit.
• Self-developed NF-κB inhibitor 270 protects against LPS-induced acute kidney injury and lung injury through improving inflammation
  作者：Yan-yan Yu、Xiang-qian Li、Wen-peng Hu、Shi-chao Cu、Jia-jia Dai、Ya-nan Gao、Yi-ting Zhang、Xiao-yi Bai、Da-yong Shi

  DOI：10.1016/j.biopha.2022.112615

  日期：2022.3