3-(3,4-二羟基苯基)-1-(4-羟基苯基)-2-丙烯-1-酮 | 88191-22-4

• 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: 3-(3,4-二羟基苯基)-1-(4-羟基苯基)-2-丙烯-1-酮
• 中文别名: 1,1'-(辛烷-1,8-二基)二[2-氨基-1,5-二氢-4H-咪唑-4-酮]
• 英文名称: 4,5,4′-trihydroxychalcone
• 英文别名: 3,4,4'-trihydroxychalcone；3,4,4'-Trihydroxy-chalkon；3,4,4'-Trihydroxychalkon；4,5,4'-Trihydroxychalcone；3-(3,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 88191-22-4；92496-89-4
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: UPERCWWUZZKHCL-UHFFFAOYSA-N

物化性质

• 沸点：
  526.4±50.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：

  3-(3,4-二羟基苯基)-1-(4-羟基苯基)-2-丙烯-1-酮 、 溶剂黄146 在 一水合肼 作用下， 以 水 为溶剂， 以40%的产率得到1-(5-(3,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone
  参考文献：
  名称：

  Design and synthesis of 3,5-diaryl-4,5-dihydro-1H-pyrazoles as new tyrosinase inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2012.12.054
• 作为产物：
  描述：

  对羟基苯乙酮 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 48.0h， 生成 3-(3,4-二羟基苯基)-1-(4-羟基苯基)-2-丙烯-1-酮
  参考文献：
  名称：

  Design, synthesis and bioactivity of chalcones and its analogues

  摘要：

  The Vernohia anthelmintica L's extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and a, beta-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a-15a, 20a and 1 b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40 mu g/mL (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2017.03.018

文献信息

• Effects of polyphenol compounds on influenza A virus replication and definition of their mechanism of action
  作者：Rossella Fioravanti、Ignacio Celestino、Roberta Costi、Giuliana Cuzzucoli Crucitti、Luca Pescatori、Leonardo Mattiello、Ettore Novellino、Paola Checconi、Anna Teresa Palamara、Lucia Nencioni、Roberto Di Santo

  DOI：10.1016/j.bmc.2012.05.062

  日期：2012.8

  A set of polyphenol compounds was synthesized and assayed for their ability in inhibiting influenza A virus replication. A sub-set of them showed low toxicity. The best compounds within this sub-set were 4 and 6g, which inhibited the viral replication in a dose-dependent manner. The antiviral activity of these molecules was demonstrated to be caused by their interference with intracellular pathways exploited for viral replication: (1) MAP kinases controlling nuclear-cytoplasmic traffic of viral ribonucleoprotein complex; (2) redox-sensitive pathways, involved in maturation of viral hemagglutinin protein. (C) 2012 Elsevier Ltd. All rights reserved.
• Klinke,P.; Gibian,H., Chemische Berichte, 1961, vol. 94, p. 26 - 38
  作者：Klinke,P.、Gibian,H.

  DOI：——

  日期：——
• 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
• Design, synthesis and bioactivity of chalcones and its analogues
  作者：Chao Niu、Adila Tuerxuntayi、Gen Li、Madina Kabas、Chang-Zhi Dong、Haji Akber Aisa

  DOI：10.1016/j.cclet.2017.03.018

  日期：2017.7

  The Vernohia anthelmintica L's extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and a, beta-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a-15a, 20a and 1 b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40 mu g/mL (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.