N-[(4'-hydroxyphenyl)methylidene]-4H-1,2,4-triazol-4-amine | 32787-78-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-[(4'-hydroxyphenyl)methylidene]-4H-1,2,4-triazol-4-amine
• 英文别名: 4-(((4H-1,2,4-triazol-4-yl)imino)methyl)phenol；4-((4H-1,2,4-triazol-4-ylimino)methyl)phenol；4-{[(4H-1,2,4-triazol-4-yl)imino]methyl}phenol；4-(1,2,4-triazol-4-yliminomethyl)phenol
• CAS: 32787-78-3
• 化学式: C₉H₈N₄O
• mdl: MFCD00463482
• 分子量: 188.189
• InChiKey: NOVRDRZKUXJKNR-UHFFFAOYSA-N

物化性质

• 熔点：
  140 °C
• 沸点：
  413.1±47.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 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-[(4'-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57%的产率得到6-(4-chlorophenyl)-2-(4-hydroxyphenyl)-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 、 对羟基苯甲醛 在 硫酸 作用下， 以 乙醇 为溶剂， 以80%的产率得到N-[(4'-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

• Triazole and Benzotriazole Derivatives as Novel Inhibitors for p90 Ribosomal S6 Protein Kinase 2: Synthesis, Molecular Docking and SAR Analysis
  作者：Jun Yuan、Ye Zhong、Shiliang Li、Xue Zhao、Guoqin Luan、Zhenjiang Zhao、Jin Huang、Honglin Li、Yufang Xu

  DOI：10.1002/cjoc.201300443

  日期：2013.7.19

  series of triazole and benzotriazole derivatives as novel p90 ribosomal S6 protein kinase 2 (RSK2) inhibitors were designed and synthesized. The in vitro activities against RSK2 were evaluated, and among 14 compounds, compounds 5, 6, 11, 12, 13 and 14 exhibited enzyme IC50 values of 8.91, 2.86, 3.19, 3.05, 4.49 and 2.09 µmol/L respectively. The proposed binding modes were simulated using molecular docking

  设计并合成了一系列三唑和苯并三唑衍生物，作为新型的p90核糖体S6蛋白激酶2（RSK2）抑制剂。在体外对RSK2活动进行了评价，并且其中14个化合物，化合物5，6，11，12，13和14显示出酶IC 50分别为8.91、2.86、3.19、3.05、4.49和2.09 µmol / L。使用分子对接方法模拟了拟议的结合模式，对接结果与结构-活性关系（SAR）分析表明，所有这些活性化合物均与NTKD上的RSK2 ATP结合位点结合，并且在电子对上具有电子给体基团。苯基的4-位是抑制活性的决定点。
• An Efficient Synthesis and Antibacterial Activity of Some Novel 2-Azetidinone Derivatives of 4H-1,2,4-Triazoles Under Mild Conditions
  作者：Takallum Khan、Ritu Yadav、Surendra Singh Gound

  DOI：10.1002/jhet.3136

  日期：2018.4

  We have synthesized the novel 2‐azetidinone derivatives by using Schiff bases of 1,2,4‐triazoles via a single step protocol. We used DABCO as a good homogenous, ecofriendly, highly reactive, easy to handle, and nontoxic catalyst. In DABCO catalyzed synthesis of active 2‐oxo‐azetidine, a highly electrophilic ketene intermediate can react with weakly nucleophilic (N═CH) linkage, which is used as the

  我们通过一步法使用1,2,4-三唑的席夫碱合成了新颖的2-氮杂环丁酮衍生物。我们使用DABCO作为良好的均质，环保，高反应性，易于处理且无毒的催化剂。在DABCO催化的活性2-氧-氮杂环丁烷的合成中，高度亲电子的乙烯酮中间体可与弱亲核（N═CH）键反应，用作环加成反应的前体，从而以质子溶剂以优异的产率提供所需的产物。另外，DABCO作为经济上可行的和容易获得的催化剂可溶于几乎所有溶剂中，并且其盐易于从反应介质中滤出。而且，这种新的合成方案具有绿色溶剂中的高转化率和简单的操作步骤的特点。
• Syntheses, in vitro α-amylase and α-glucosidase dual inhibitory activities of 4-amino-1,2,4-triazole derivatives their molecular docking and kinetic studies
  作者：Emmanuel Oloruntoba Yeye、Kanwal、Khalid. Mohammed Khan、Sridevi Chigurupati、Abdul Wadood、Ashfaq Ur Rehman、Shahnaz Perveen、Mari Kannan Maharajan、Shahbaz Shamim、Shehryar Hameed、Sherifat A. Aboaba、Muhammad Taha

  DOI：10.1016/j.bmc.2020.115467

  日期：2020.6

  for their anti-hyperglycemic potential. Compounds 1-33 exhibited good to moderate in vitro α-amylase and α-glucosidase inhibitory activities in the range of IC50 values 2.01 ± 0.03-6.44 ± 0.16 and 2.09 ± 0.08-6.54 ± 0.10 µM as compared to the standard acarbose (IC50 = 1.92 ± 0.17 µM) and (IC50 = 1.99 ± 0.07 µM), respectively. The limited structure-activity relationship suggested that different substitutions

  通过使4-氨基-1,2,4-三唑与多种苯甲醛反应合成了33种4-氨基-1,2,4-三唑衍生物1-33。合成分子通过1 H NMR和EI-MS光谱技术进行表征，并评估其抗高血糖的潜力。与标准阿卡波糖相比，化合物1-33在IC50值范围为2.01±0.03-6.44±0.16和2.09±0.08-6.54±0.10 µM的范围内，具有良好至中等的体外α-淀粉酶和α-葡萄糖苷酶抑制活性。 1.92±0.17 µM）和（IC50 = 1.99±0.07 µM）。有限的结构活性关系表明，合成化合物芳基部分的不同取代是造成可变活性的原因。动力学研究预测，化合物1-33分别受到混合和非竞争性抑制α-淀粉酶和α-葡萄糖苷酶的作用。在计算机研究中，三唑和芳基环以及不同的取代在酶口袋内抑制剂的结合相互作用中起着重要作用。已发现合成分子对两种酶均具有双重抑制潜能，因此它们可作为药物开发和未来研究的主要候选对象。
• 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.