N-[(5'-bromo-2'-hydroxyphenyl)methylidene]-4H-1,2,4-triazol-4-amine | 294853-17-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-[(5'-bromo-2'-hydroxyphenyl)methylidene]-4H-1,2,4-triazol-4-amine
• 英文别名: 4-Bromo-2-(1,2,4-triazol-4-yliminomethyl)phenol
• CAS: 294853-17-1
• 化学式: C₉H₇BrN₄O
• mdl: MFCD00513966
• 分子量: 267.085
• InChiKey: ZNJKBUYYFGCGNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 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：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(5'-bromo-2'-hydroxyphenyl)methylidene]-4H-1,2,4-triazol-4-amine 、 异硫氰酸 p-氯苯甲酰脂 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以53%的产率得到2-(5-bromo-2-hydroxyphenyl)-6-(4-chlorophenyl)-3-(1,2,4-triazol-4-yl)-2H-1,3,5-oxadiazine-4-thione
  参考文献：
  名称：

  Synthesis and Biological Activity of 3-[4H-(1,2,4)-Triazolyl]-2,6-diaryl-1,3,5-oxadiazine-4-thione

  摘要：

  4-Amino-1,2,4-triazole (1) undergoes facile condensation with aromatic aldehydes to afford the corresponding 4-(arylidene-amino)-4H-[1,2,4]-triazole (2a-h) in good yield. Rearrangement of compounds (2a-h) with benzoyl isothiocyanate/4-chlorobenzoyl isothiocyanate/2,4-dichloro-benzoyl isothiocyanate yields corresponding 1,3,5-oxadiazine derivatives (3). Structural elucidation of these compounds was based on elementary analysis and spectral data studies. The newly synthesized compounds were evaluated for their antibacterial activities.

  DOI：

  10.1080/10426500802487789
• 作为产物：
  描述：

  4-氨基-1,2,4-三氮唑 、 5-溴水杨醛 在 硫酸 作用下， 以 乙醇 为溶剂， 以81%的产率得到N-[(5'-bromo-2'-hydroxyphenyl)methylidene]-4H-1,2,4-triazol-4-amine
  参考文献：
  名称：

  三唑席夫氏碱对果糖介导的糖基化的抗糖化活性：体外和计算机模拟研究。

  摘要：

  背景：已知晚期糖基化终产物（AGEs）与糖尿病并发症，神经退行性疾病和衰老的病理生理有关。预防AGEs的形成可能有助于控制这些疾病。 目的：评估了两类先前合成的曲唑席夫碱（4H-1,2,4-三唑-4-席夫碱1-14和4H-1,2,4-三唑-3-席夫碱15-23）。具有体外抗糖化活性 方法：采用果糖介导的人血清白蛋白（HSA）糖基化体外试验来评估三唑席夫碱的抗糖化活性。通过MTT测定法对小鼠成纤维细胞（3T3）细胞系上的活性化合物进行细胞毒性分析。进行了分子对接和模拟研究，以评估化合物与HSA的相互作用和稳定性。分别通过体外α-葡萄糖苷酶抑制作用和DPPH自由基清除试验评估了选定的非细胞毒性化合物的抗高血糖和抗氧化活性。 结果：来自4H-1,2,4-三唑-4-席夫碱的化合物1（IC50 = 47.30±0.38 µM）具有与标准芦丁（IC50 = 54.5±0.05 µM）相当的抗糖化活性，

  DOI：

  10.2174/1573406415666190212105718

文献信息

• 1,2,4-Triazole-based molecular switches: crystal structures, Hirshfeld surface analysis and optical properties
  作者：Damir A. Safin、Koen Robeyns、Yann Garcia

  DOI：10.1039/c6ce00749j

  日期：——

  established that the crystal structures of 5–8 each are stabilized by a linear intramolecular hydrogen bond of the O–H⋯N type, formed between the o-OH hydrogen atom of the phenolic ring and the imine nitrogen atom. The same o-OH function in the crystal structures of 1–4 was found to be involved in the intermolecular hydrogen bonds with one of the triazole nitrogen atoms of the adjacent molecule. The overall

  我们研究了一系列八个紧密相关的N-水杨基亚烷基-4-氨基-1,2,4-三唑分子1-8，这些分子是通过将相应的醛与4-氨基-4 H -1,2,4-缩合而获得的。三唑。溶液中的1 H NMR光谱显示至少在DMSO- d 6中存在单个结构。根据单晶X射线衍射，可以确定，每个5-8的晶体结构都通过在酚的邻位-OH氢原子之间形成的O-H⋯N型线性分子内氢键来稳定环和亚胺氮原子。1-4的晶体结构中具有相同的o -OH功能据发现，其与相邻分子的三唑氮原子之一参与分子间氢键。发现每个分子在1–8的结构中的总体几何形状几乎是平面的，或者略微偏离平面度。Hirshfeld表面分析表明，所有化合物的结构主要以H⋯H，H⋯C，H⋯N和H⋯O接触为特征，但也清楚地观察到C⋯C和C⋯N接触的一些贡献。漫反射光谱法显示，在室温下，固态和单独存在的烯醇形式分别为1–6和8，而显性烯醇和顺式酮形式的混合物则存在7。所有研究
• Synthesis and Biological Activity of 3-[4<i>H</i>-(1,2,4)-triazolyl]-2-aryl-1,3-thiazolidin-4-ones
  作者：H. S. Patel、K. B. Patel

  DOI：10.1080/10426500801963772

  日期：2008.9.15

  4-Amino-1,2,4-triazole (1) undergoes facile condensation with aromatic aldehydes to afford the corresponding 4-(arylidene-amino)-4H-[1,2,4]-triazole (2 a-h) in good yields. Cyclocondensation of compounds (2 a-h) with thioglycolic acid yields 3-[4H-(1,2,4)-triazolyl]-2-aryl-1,3-thiazolidin-4-ones (3 a-h). The structures of these compounds were established on the basis of analytical and spectral data. The newly synthesized compounds were evaluated for their antibacterial and antifungal activities.
• Synthesis of triazole Schiff bases: Novel inhibitors of nucleotide pyrophosphatase/phosphodiesterase-1
  作者：Khalid Mohammed Khan、Salman Siddiqui、Muhammad Saleem、Muhammad Taha、Syed Muhammad Saad、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1016/j.bmc.2014.08.032

  日期：2014.11

  A series of Schiff base triazoles 1-25 was synthesized and evaluated for their nucleotide pyrophosphatase/ phosphodiesterase-1 inhibitory activities. Among twenty-five compounds, three compounds 10 (IC50 = 132.20 +/- 2.89 mu M), 13 (IC50 = 152.83 +/- 2.39 mu M), and 22 (IC50 = 251.0 +/- 6.64 mu M) were identified as potent inhibitors with superior activities than the standard EDTA (IC50 = 277.69 +/- 2.52 mu M). The newly identified inhibitors may open a new avenue for the development of treatment of phosphodiesterase-I related disorders. These compounds were also evaluated for carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase inhibitory potential and were found to be inactive. The compounds showed non-toxic effect towards PC3 cell lines. (C) 2014 Elsevier Ltd. All rights reserved.