5-(3,4,5-trihydroxybenzylidene)-2,4,6(1H,3H,5H)-pyrimidinetrione

• 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-(3,4,5-trihydroxybenzylidene)-2,4,6(1H,3H,5H)-pyrimidinetrione
• 英文别名: 5-(3,4,5-trihydroxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione；5-[(3,4,5-Trihydroxyphenyl)methylene]hexahydropyrimidine-2,4,6-trione；5-[(3,4,5-trihydroxyphenyl)methylidene]-1,3-diazinane-2,4,6-trione
• 化学式: C₁₁H₈N₂O₆
• 分子量: 264.194
• InChiKey: OWZNXHRLWKYIQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 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：
  136
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  巴比妥酸 、 3,4,5-三羟基苯甲醛 在 氯化铵 作用下， 以 水 为溶剂， 反应 0.5h， 以93%的产率得到5-(3,4,5-trihydroxybenzylidene)-2,4,6(1H,3H,5H)-pyrimidinetrione
  参考文献：
  名称：

  NH4Cl Mediated New Protocol for the Synthesis of 5-Arylidene Barbiturates

  摘要：

  已经开发了一种生态友好的合成苯偶氮巴比妥酸酯的方法，使用氯化铵（NH4Cl）作为等摩尔反应活化剂，在水中进行。该方法简单，产品产率高，反应在30分钟内完成。这种新方法不涉及任何溶剂或溶剂萃取，所有情况下均产生固体产品，这些产品经过过滤和洗涤。

  DOI：

  10.2174/157017811794557778

文献信息

• NH4Cl Mediated New Protocol for the Synthesis of 5-Arylidene Barbiturates
  作者：Khalid Mohammed Khan、Muhammad Ali、Momin Khan、Muhammad Taha、Shahnaz Perveen

  DOI：10.2174/157017811794557778

  日期：2011.1.1

  Eco-benign method for synthesizing arylidene barbiturates has been developed by using ammonium chloride (NH4Cl) in stoichiometric amount, as an enolization activator, in water. Execution of methodology is simple, products obtained in high yields and the reactions are completed within 30 min. The new methodology does not involve any solvent/solvent extraction while solid products were yielded in all cases which were filtered and washed.

  已经开发了一种生态友好的合成苯偶氮巴比妥酸酯的方法，使用氯化铵（NH4Cl）作为等摩尔反应活化剂，在水中进行。该方法简单，产品产率高，反应在30分钟内完成。这种新方法不涉及任何溶剂或溶剂萃取，所有情况下均产生固体产品，这些产品经过过滤和洗涤。
• 2,6-Bis(3,4,5-trihydroxybenzylydene) derivatives of cyclohexanone
  作者：Roberta Costi、Roberto Di Santo、Marino Artico、Silvio Massa、Rino Ragno、Roberta Loddo、Massimiliano La Colla、Enzo Tramontano、Paolo La Colla、Alessandra Pani

  DOI：10.1016/j.bmc.2003.10.005

  日期：2004.1

  A number of 2,6-bisbenzylidenecyclohexane-1-one derivatives have been synthesized and tested as HIV-1 integrase (IN) inhibitors with the aim of obtaining compounds capable to elicit antiviral activity at non-cytotoxic concentrations in cell-based assays. 3,5-Bis(3,4,5-trihydroxybenzylidene)-4-oxocyclohexaneacetic acid (20d) resulted one of the most potent and selective derivatives in acutely infected MT-4 cells (EC50 and CC50 values of 2 and 40 muM, respectively). In enzyme assays with recombinant HIV-1 integrase (rIN), this compound proved able to inhibit both 3'-processing and disintegration with IC50 values of 0.2 and 0.5 muM, respectively. In order to develop a model capable to predict the anti HIV-IN activity and useful to design novel derivatives, we performed a comparative molecular field analysis (CoMFA) like 3-D-QSAR. In our model the ligands were described quantitatively in the GRID program, and the model was optimized by selecting only the most informative variables in the GOLPE program. We found the predictive ability of the model to increase significantly when the number of variables was reduced from 20,925 to 1327. A Q(2) of 0.73 was obtained with the final model, confirming the predictive ability of the model. By studying the PLS coefficients in informative 3-D contour plots, ideas for the synthesis of new compounds could be generated. (C) 2003 Elsevier Ltd. All rights reserved.
• Khan, Khalid Mohammed; Ali, Muhammad; Ahmad, Aqeel, Journal of the Chemical Society of Pakistan, 2013, vol. 35, # 3, p. 890 - 893
  作者：Khan, Khalid Mohammed、Ali, Muhammad、Ahmad, Aqeel、Amyn, Afroze、Karim, Aneela、Khan, Momin、Parveen, Shahnaz

  DOI：——

  日期：——
• 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.