5-(4-(2-(2-methoxyethoxy)ethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione | 1189045-06-4

• 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-(4-(2-(2-methoxyethoxy)ethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
• 英文别名: 5-[[4-[2-(2-methoxyethoxy)ethoxy]phenyl]methylidene]-1,3-diazinane-2,4,6-trione
• CAS: 1189045-06-4
• 化学式: C₁₆H₁₈N₂O₆
• 分子量: 334.329
• InChiKey: UITURPDFKUCROB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(4-(2-(2-methoxyethoxy)ethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以82%的产率得到5-(4-(2-(2-methoxyethoxy)ethoxy)benzyl)pyrimidine-2,4,6(1H,3H,5H)trione
  参考文献：
  名称：

  Inhibitory effects of 5-benzylidene barbiturate derivatives on mushroom tyrosinase and their antibacterial activities

  摘要：

  A series of novel 5-benzylidene barbiturate and thiobarbiturate derivatives were synthesized and evaluated as tyrosinase inhibitors and antibacterial agents. The results demonstrated that some compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC50 = 1.22 mM). Particularly, compounds 1a and 2a were found to be the most potent inhibitors with IC50 value of 13.98 mu M and 14.49 mu M, respectively. The inhibition mechanism study revealed that these compounds were irreversible inhibitors. The circular dichroism spectra indicated that these compounds induced conformational changes of mushroom tyrosinase upon binding. In addition, these compounds exhibited selectively antibacterial activity against Staphylococcus aureus. All these results suggested that further development of such compounds may be of interest. (c) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.05.023
• 作为产物：
  描述：

  巴比妥酸 、 4-[2-(2-甲氧基乙氧基)乙氧基]苯甲醛 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到5-(4-(2-(2-methoxyethoxy)ethoxy)benzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  Inhibitory effects of 5-benzylidene barbiturate derivatives on mushroom tyrosinase and their antibacterial activities

  摘要：

  A series of novel 5-benzylidene barbiturate and thiobarbiturate derivatives were synthesized and evaluated as tyrosinase inhibitors and antibacterial agents. The results demonstrated that some compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC50 = 1.22 mM). Particularly, compounds 1a and 2a were found to be the most potent inhibitors with IC50 value of 13.98 mu M and 14.49 mu M, respectively. The inhibition mechanism study revealed that these compounds were irreversible inhibitors. The circular dichroism spectra indicated that these compounds induced conformational changes of mushroom tyrosinase upon binding. In addition, these compounds exhibited selectively antibacterial activity against Staphylococcus aureus. All these results suggested that further development of such compounds may be of interest. (c) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.05.023

文献信息

• Inhibitory effects of 5-benzylidene barbiturate derivatives on mushroom tyrosinase and their antibacterial activities
  作者：Qin Yan、Rihui Cao、Wei Yi、Zhiyong Chen、Huan Wen、Lin Ma、Huacan Song

  DOI：10.1016/j.ejmech.2009.05.023

  日期：2009.10

  A series of novel 5-benzylidene barbiturate and thiobarbiturate derivatives were synthesized and evaluated as tyrosinase inhibitors and antibacterial agents. The results demonstrated that some compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC50 = 1.22 mM). Particularly, compounds 1a and 2a were found to be the most potent inhibitors with IC50 value of 13.98 mu M and 14.49 mu M, respectively. The inhibition mechanism study revealed that these compounds were irreversible inhibitors. The circular dichroism spectra indicated that these compounds induced conformational changes of mushroom tyrosinase upon binding. In addition, these compounds exhibited selectively antibacterial activity against Staphylococcus aureus. All these results suggested that further development of such compounds may be of interest. (c) 2009 Elsevier Masson SAS. All rights reserved.