5-((2-nitrophenyl)diazenyl)pyrimidine-2,4,6-triamine | 119406-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-((2-nitrophenyl)diazenyl)pyrimidine-2,4,6-triamine
• 英文别名: 5-[(2-Nitrophenyl)diazenyl]pyrimidine-2,4,6-triamine
• CAS: 119406-43-8
• 化学式: C₁₀H₁₀N₈O₂
• 分子量: 274.242
• InChiKey: WBLQBTKNPAHMQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  174
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-((2-nitrophenyl)diazenyl)pyrimidine-2,4,6-triamine 在 碘苯二乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以84%的产率得到2-(2-Nitrophenyl)triazolo[4,5-d]pyrimidine-5,7-diamine
  参考文献：
  名称：

  Substituted tetraazapentalenes

  摘要：

  替代四氮杂戊烯具有两个苯环和八个可替换位置。可以用氨基、硝基或氮原子替换氢或C-H基团。四氮杂戊烯是通过中间体偶氮化合物合成的，该偶氮化合物由1:1:1摩尔比的硝基苯胺、亚硝酸钠和胺制备而成。

  公开号：

  US08273877B1
• 作为产物：
  描述：

  2,4,6-三氨基嘧啶 、 2-硝基苯胺 在 盐酸 、 sodium nitrite 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 以90%的产率得到5-((2-nitrophenyl)diazenyl)pyrimidine-2,4,6-triamine
  参考文献：
  名称：

  Substituted tetraazapentalenes

  摘要：

  替代四氮杂戊烯具有两个苯环和八个可替换位置。可以用氨基、硝基或氮原子替换氢或C-H基团。四氮杂戊烯是通过中间体偶氮化合物合成的，该偶氮化合物由1:1:1摩尔比的硝基苯胺、亚硝酸钠和胺制备而成。

  公开号：

  US08273877B1

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.
• Substituted tetraazapentalenes
  申请人：The United States of America as Represented by the Secretary of the Navy

  公开号：US08273877B1

  公开（公告）日：2012-09-25

  Substituted tetraazapentalenes have two benzenoid rings and eight substitutable positions. Substitutions are made of hydrogen or C—H groups in favor of amino groups, nitro groups or nitrogen atoms. The tetraazapentalenes are synthesized through an intermediate azo, which is made from a 1:1:1 molar ratio of a nitroaniline, sodium nitrite and an amine.

  替代四氮杂戊烯具有两个苯环和八个可替换位置。可以用氨基、硝基或氮原子替换氢或C-H基团。四氮杂戊烯是通过中间体偶氮化合物合成的，该偶氮化合物由1:1:1摩尔比的硝基苯胺、亚硝酸钠和胺制备而成。