1-(3-(2,4-dihydroxyphenyl)-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one | 1428324-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(3-(2,4-dihydroxyphenyl)-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one
• 英文别名: 1-[5-(2,4-Dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone；1-[5-(2,4-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
• CAS: 1428324-85-9
• 化学式: C₁₈H₁₈N₂O₅
• 分子量: 342.351
• InChiKey: YLYVYODJVSVBNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  香草醛 在 aluminum oxide 、 一水合肼 、 potassium hydroxide 作用下， 以 水 为溶剂， 生成 1-(3-(2,4-dihydroxyphenyl)-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one
  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

文献信息

• Discovery of isoliquiritigenin analogues that reverse acute hepatitis by inhibiting macrophage polarization
  作者：Junjie Yang、Fanjie Hu、Chengjun Guo、Yuqing Liang、Haiying Song、Kui Cheng

  DOI：10.1016/j.bioorg.2021.105043

  日期：2021.9
• 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.