5-(2,4,6-trihydroxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione | 1610969-23-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(2,4,6-trihydroxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
• 英文别名: 2-Sulfanylidene-5-[(2,4,6-trihydroxyphenyl)methylidene]-1,3-diazinane-4,6-dione；2-sulfanylidene-5-[(2,4,6-trihydroxyphenyl)methylidene]-1,3-diazinane-4,6-dione
• CAS: 1610969-23-7
• 化学式: C₁₁H₈N₂O₅S
• 分子量: 280.261
• InChiKey: UNPPHIHAGVDIMU-UHFFFAOYSA-N

物化性质

• 熔点：
  250 °C
• 密度：
  1.837±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  151
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,6-二羟基-2-巯基嘧啶 、 间苯三酚甲醛 以 乙醇 为溶剂， 反应 2.0h， 以57%的产率得到5-(2,4,6-trihydroxybenzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
  参考文献：
  名称：

  Design, synthesis and biological evaluation of hydroxy- or methoxy-substituted 5-benzylidene(thio) barbiturates as novel tyrosinase inhibitors

  摘要：

  Here a new class of hydroxy- or methoxy-substituted 5-benzylidene(thio)barbiturates were designed, synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that several compounds had more potent tyrosinase inhibitory activities than the widely used tyrosinase inhibitor kojic acid (IC50 = 18.25 mu M). In particular, 3',4'-dihydroxylated 1e was found to be the most potent inhibitor with IC50 value of 1.52 mu M. The inhibition mechanism analysis revealed that the potential compounds 1e and 2e exhibited such inhibitory effects on tyrosinase by acting as the irreversible inhibitors. Structure-activity relationships' (SARs) analysis also suggested that further development of such compounds might be of interest. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.060

文献信息

• Design, synthesis and biological evaluation of hydroxy- or methoxy-substituted 5-benzylidene(thio) barbiturates as novel tyrosinase inhibitors
  作者：Zhiyong Chen、Dachuan Cai、Dehai Mou、Qin Yan、Yifeng Sun、Wenlong Pan、Yiqian Wan、Huacan Song、Wei Yi

  DOI：10.1016/j.bmc.2014.04.060

  日期：2014.7

  Here a new class of hydroxy- or methoxy-substituted 5-benzylidene(thio)barbiturates were designed, synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that several compounds had more potent tyrosinase inhibitory activities than the widely used tyrosinase inhibitor kojic acid (IC50 = 18.25 mu M). In particular, 3',4'-dihydroxylated 1e was found to be the most potent inhibitor with IC50 value of 1.52 mu M. The inhibition mechanism analysis revealed that the potential compounds 1e and 2e exhibited such inhibitory effects on tyrosinase by acting as the irreversible inhibitors. Structure-activity relationships' (SARs) analysis also suggested that further development of such compounds might be of interest. (C) 2014 Elsevier Ltd. All rights reserved.