2''-methoxy-2',4''-dihydroxychalcone | 1428324-82-6

• 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
• 英文名称: 2''-methoxy-2',4''-dihydroxychalcone
• 英文别名: 2',4-Dihydroxy-6-methoxy-chalcone；3-(4-hydroxy-2-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 1428324-82-6
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: HXBNENMARBAMFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2''-methoxy-2',4''-dihydroxychalcone 、 溶剂黄146 在 一水合肼 作用下， 以 水 为溶剂， 以42%的产率得到1-[3-(4-Hydroxy-2-methoxyphenyl)-5-(2-hydroxyphenyl)-3,4-dihydropyrazol-2-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：

  4-羟基-2-甲氧基苯甲醛 、 2'-羟基苯乙酮 在 aluminum oxide 、 potassium hydroxide 作用下， 生成 2''-methoxy-2',4''-dihydroxychalcone
  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

• 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.