5-(p-tolyldiazenyl)pyrimidine-2,4,6-triamine | 32606-22-7

• 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-(p-tolyldiazenyl)pyrimidine-2,4,6-triamine
• 英文别名: 2,4,6-Triamino-5-p-tolylazo-pyrimidin；5-p-tolylazo-pyrimidine-2,4,6-triamine；5-[(4-Methylphenyl)diazenyl]pyrimidine-2,4,6-triamine
• CAS: 32606-22-7
• 化学式: C₁₁H₁₃N₇
• 分子量: 243.271
• InChiKey: URNNLVYOUGSLIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,4,6-三氨基嘧啶 、 乙烷,三氯氟- 在 硫酸 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以83%的产率得到5-(p-tolyldiazenyl)pyrimidine-2,4,6-triamine
  参考文献：
  名称：

  新型嘧啶衍生物作为新型蘑菇酪氨酸酶抑制剂的评价

  摘要：

  Background and aim: Tyrosinase (EC 1.14.18.1) is responsible for enzymatic browning in fruits and vegetables. Its inhibitors may be applied to efficiently treat hyperpigmentation and are widely used in pharmaceutical and cosmetic products, food supplements and insecticides. Previous studies have shown that heterocyclic compounds with an amino group can inhibit tyrosinase activity. The present study aims to evaluate the inhibitory effect of some novel 2,6-diamino-4-chloropyrimidine derivatives (la-e) and 2,4,6-triaminopyrimidine (2a-e) including bioactive aniline moiety on the activity of the mushroom tyrosinase.Methods: In practice, the azo salt was initially synthesized from aniline derivatives and combined subsequently with the 2,4,6-triaminopyrimidine and 2,6-diamino-4 chloropyrimidine followed by crystallization. The structures of resulting compounds were confirmed by FT-IR, C-13 NMR, and H-1 NMR. The derivatives (0-100 mu M) were evaluated for their inhibitory effect on tyrosinase activity using 1-3,4-dihydroxyphenylalanine (1-DOPA) as substrate.Results: All compounds showed inhibitory effects against the activity of the enzyme. About 23.72-55.08% inhibition was observed in the presence of 30 mu M of each compound. The IC50 values of the synthesized compounds were measured, and their inhibition properties were also visualized by zymography. Based on the results, the compounds 1a-e and 2a-e showed moderate inhibitory activities. Notably, pyrimidine derivatives 1a (IC50=24.68) and 1d (IC50=24.45) also exhibited similar inhibitory activities when compared with the positive control, kojic acid (IC50=25.24 mu M). Kinetic studies indicated that the type of inhibition was noncompetitive.Conclusion: All results suggest that pyrimidine derivatives, especially 1d and 1a, can be considered as safe and efficient tyrosinase inhibitors.

  DOI：

  10.2147/dddt.s209324

文献信息

• Studies on the series of azoles and azines. 66. Synthesis, spectra and structure of 5-arylazo- and 5-arylideneamino-2,4,6-triaminopyrimidines and their 6-hydroxy analogs
  作者：Zh. V. Belodedova、N. A. Smorygo、V. S. Mirzoyan、R. G. Melik-Orandzhanyan、E. P. Studentsov、B. A. Ivin

  DOI：10.1007/bf00755696

  日期：1988.5
• <p>Evaluation of novel pyrimidine derivatives as a new class of mushroom tyrosinase inhibitor</p>
  作者：S Shohreh Mirmortazavi、Mahdieh Farvandi、Hossein Ghafouri、Asadollah Mohammadi、Mostafa Shourian

  DOI：10.2147/dddt.s209324

  日期：——

  Background and aim: Tyrosinase (EC 1.14.18.1) is responsible for enzymatic browning in fruits and vegetables. Its inhibitors may be applied to efficiently treat hyperpigmentation and are widely used in pharmaceutical and cosmetic products, food supplements and insecticides. Previous studies have shown that heterocyclic compounds with an amino group can inhibit tyrosinase activity. The present study aims to evaluate the inhibitory effect of some novel 2,6-diamino-4-chloropyrimidine derivatives (la-e) and 2,4,6-triaminopyrimidine (2a-e) including bioactive aniline moiety on the activity of the mushroom tyrosinase.Methods: In practice, the azo salt was initially synthesized from aniline derivatives and combined subsequently with the 2,4,6-triaminopyrimidine and 2,6-diamino-4 chloropyrimidine followed by crystallization. The structures of resulting compounds were confirmed by FT-IR, C-13 NMR, and H-1 NMR. The derivatives (0-100 mu M) were evaluated for their inhibitory effect on tyrosinase activity using 1-3,4-dihydroxyphenylalanine (1-DOPA) as substrate.Results: All compounds showed inhibitory effects against the activity of the enzyme. About 23.72-55.08% inhibition was observed in the presence of 30 mu M of each compound. The IC50 values of the synthesized compounds were measured, and their inhibition properties were also visualized by zymography. Based on the results, the compounds 1a-e and 2a-e showed moderate inhibitory activities. Notably, pyrimidine derivatives 1a (IC50=24.68) and 1d (IC50=24.45) also exhibited similar inhibitory activities when compared with the positive control, kojic acid (IC50=25.24 mu M). Kinetic studies indicated that the type of inhibition was noncompetitive.Conclusion: All results suggest that pyrimidine derivatives, especially 1d and 1a, can be considered as safe and efficient tyrosinase inhibitors.