5-(2-硝基苯基)-4H-1,2,4-三唑-3-胺 | 59301-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(2-硝基苯基)-4H-1,2,4-三唑-3-胺
• 英文名称: 3-Amino-5-o-nitrophenyl-1,2,4-triazol
• 英文别名: 5(3)-(2-Nitrophenyl)-3(5)amino-1,2,4-triazol；5-(2-nitro-phenyl)-1H-[1,2,4]triazol-3-ylamine；5-(2-nitrophenyl)-1H-1,2,4-triazol-3-amine
• CAS: 59301-22-3
• 化学式: C₈H₇N₅O₂
• 分子量: 205.176
• InChiKey: OXVOSTFDRAAYSZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.535

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 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：
  113
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(2-硝基苯基)-4H-1,2,4-三唑-3-胺 在 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-(2-nitrophenyl)-5-(methylthio)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-one
  参考文献：
  名称：

  Synthesis, anti-thymidine phosphorylase activity and molecular docking of 5-thioxo-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ones

  摘要：

  In our lead finding program, a series of 5-thioxo-[1,2,4] triazolo[1,5-a][1,3,5]triazin-7-ones and their 5-thio- alkyl derivatives were designed and synthesized which contained different substituents at ortho-position of 2-phenyl ring attached to the fused ring structure. The preliminary pharmacological evaluation demonstrated that the synthesized compounds exhibited a varying degree of inhibitory activity towards thymidine phosphorylase (TP), comparable to reference compound, 7-Deazaxanthine (7-DX, 2) (IC50 value = 42.63 mu M). The study also inferred that the ortho-substituted group at the phenyl ring and 5-thio-alkyl moiety imparted steric hindrance effects in the binding site of the enzyme, leading to a reduced inhibitory response. In addition, compound 3a was identified as a mixed-type inhibitor of TP. Moreover, computational docking study was performed to illustrate the important structural information on the plausible ligand-enzyme binding interactions. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.07.004
• 作为产物：
  描述：

  邻硝基苯甲醛 在 三氟化硼乙醚 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 0.5h， 生成 5-(2-硝基苯基)-4H-1,2,4-三唑-3-胺
  参考文献：
  名称：

  Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N-Tosylhydrazones

  摘要：

  DOI：

  10.1021/acs.orglett.1c01379

文献信息

• A Novel Iron-catalyzed One-pot Synthesis of 3-Amino-1,2,4-triazoles
  作者：Taoufik Rohand、Victor N. Mkpenie、Mohammadine El Haddad、István E. Markó

  DOI：10.1002/jhet.3450

  日期：2019.2

  A novel one‐pot synthesis of 3‐amino‐1,2,4‐triazole developed via iron (III) catalyzed route is reported. The new method is more efficient, simple, and convenient and presents a concise new strategy for the synthesis of 3‐amino‐1,2,4‐triazole derivatives. The iron (III) complex intermediate assisted in the intramolecular bond cyclization owing to its Lewis acidity or oxidizing properties. A series

  据报道，通过铁（III）催化途径开发的一种新型一锅法合成3-氨基1,2,4-三唑。该新方法更加高效，简单和方便，为合成3‐氨基1,2,4‐三唑衍生物提出了一种简洁的新策略。铁（III）配合物中间体由于其路易斯酸度或氧化特性而有助于分子内键的环化。还研究了一系列在对位和/或邻位带有取代的给电子和吸电子基团的芳族腈。取代基的位置影响最终化合物的收率，对位取代的底物收率相对较高。
• Phosphorylation of 5-Amino-1H-1,2,4-triazoles with Diethyl Phosphorochloridate
  作者：D. Yu. Voronina、A. S. Krylov、V. V. Tolstyakov、A. V. Dogadina

  DOI：10.1134/s1070363224010067

  日期：2024.1

  Abstract New phosphorylated 5-amino-1H-1,2,4-triazoles were obtained by the chemoselective reaction of diethyl phosphorochloridate with 5-amino-1H-1,2,4-triazoles. The structure of the synthesized compounds was characterized by 1H, 13C, and 31P NMR spectroscopy and mass spectrometry.

  摘要 通过氯代磷酸二乙酯与5-氨基-1 H -1,2,4-三唑的化学选择性反应得到新的磷酸化5-氨基-1 H -1,2,4-三唑。合成化合物的结构通过1 H、13 C 和31 P NMR 光谱和质谱进行表征。