5-(2-溴苯基)-4H-1,2,4-三唑-3-胺 | 59301-25-6

• 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-溴苯基)-4H-1,2,4-三唑-3-胺
• 英文名称: 3-Amino-5-o-bromphenyl-1,2,4-triazol
• 英文别名: 5(3)-(2-Bromphenyl)-3(5)amino-1,2,4-triazol；5-(2-bromo-phenyl)-1H-[1,2,4]triazol-3-ylamine；5-(2-bromophenyl)-1H-1,2,4-triazol-3-amine
• CAS: 59301-25-6
• 化学式: C₈H₇BrN₄
• mdl: MFCD04966855
• 分子量: 239.074
• InChiKey: CXRHBUWCLZAXAC-UHFFFAOYSA-N

物化性质

• 密度：
  1.732

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 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：
  67.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-(2-溴苯基)-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-bromophenyl)-5-thioxo-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-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：

  2-溴苯甲酰肼 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 5-(2-溴苯基)-4H-1,2,4-三唑-3-胺
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of tricyclic derivatives as selective RXFP4 agonists

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104782

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。
• Synthesis of New Fluorine Containing Triazolo- and Tetrazolopyrimidines
  作者：Arcady L. Krasovsky、Andrew M. Moiseev、Valentine G. Nenajdenko、Elizabeth S. Balenkova

  DOI：10.1055/s-2002-28512

  日期：——

  reaction of 1,1,1-trifluoro-4-(sulfonyl)-but-3-ene-2,2-dioles 1a,b with corresponding aminoazoles was investigated. A new simple and efficient way for the regioselective synthesis of 5-CF 3 or 7-CF 3 triazolo- and tetrazolopyrimidines is described.

  研究了 1,1,1-trifluoro-4-(sulfonyl)-but-3-ene-2,2-dioles 1a,b 与相应的氨基唑的反应。描述了一种新的简单有效的区域选择性合成 5-CF 3 或 7-CF 3 三唑并四唑嘧啶的方法。
• Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from <i>N</i>-Tosylhydrazones
  作者：Zeyang Wei、Qi Zhang、Meng Tang、Siyu Zhang、Qian Zhang

  DOI：10.1021/acs.orglett.1c01379

  日期：2021.6.4