2-[(1H-1,2,4-triazol-3-ylimino)methyl]phenol | 24829-12-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[(1H-1,2,4-triazol-3-ylimino)methyl]phenol
• 英文别名: salicylidene-3-amino-1,2,4-triazole；2-(1H-1,2,4-triazol-5-yliminomethyl)phenol
• CAS: 24829-12-7
• 化学式: C₉H₈N₄O
• mdl: MFCD00187081
• 分子量: 188.189
• InChiKey: BKYHBHVZLQLDIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  74.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(1H-1,2,4-triazol-3-ylimino)methyl]phenol 、 cobalt(II) chloride 以 乙醇 为溶剂， 反应 2.0h， 以75%的产率得到
  参考文献：
  名称：

  Scrutinizing the DNA damaging and antimicrobial abilities of triazole appended metal complexes

  摘要：

  New mononuclear transition metal complexes 1-12 bearing the bioactive triazole analogues were synthesized and characterized by elemental analysis and spectroscopic techniques. The interaction of calf thymus DNA (CT-DNA) with the synthesized compounds was studied at physiological pH by spectrophotometric, spectrofluorometric, cyclic voltammetry, and viscometric techniques. The entire DNA binding results suggested the intercalative mode of binding for the synthesized compounds. Interestingly, the binding strength of the complexes is found to be greater than that of the free ligands. Among the complexes explored, complex 5 reveals strong hypochromism and a slight red shift as compared to the other complexes highlighting its higher DNA binding propensity. The intrinsic binding constant values of the complexes compared to cisplatin reveal that all the complexes are greater in magnitude than that of cisplatin. Fluorescence titrations show that the Cu(II) complexes have the ability to displace DNA-bound ethidium bromide. Also, these compounds induce cleavage in pBR322 plasmid DNA as indicated in gel electrophoresis and exhibit excellent nuclease activity in the presence of H2O2. Moreover, the complexes were screened for in vitro antimicrobial activity along with free ligands and solvent control. The outcome is that the complexes possess good activity than the free ligands. These complexes may have further scope in developing them into antimicrobial drugs and DNA probes. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotobiol.2016.02.033
• 作为产物：
  描述：

  3-氨基-1,2,4-三氮唑 、 水杨醛 以 甲醇 为溶剂， 反应 0.5h， 生成 2-[(1H-1,2,4-triazol-3-ylimino)methyl]phenol
  参考文献：
  名称：

  3-氨基-1H-1,2,4-三唑衍生席夫碱的结构研究

  摘要：

  摘要 本文合成了12 种源自3-氨基-1H-1,2,4-三唑(ATz) 和各种苯甲醛和水杨醛的席夫碱。1H、13C 和 15N NMR 数据与 ATz 及其亚胺产物的结构有关。此外，X 射线、ATR-FTIR 和 UV-Vis 分析技术用于基于 ATz 的 Schiff 碱的结构解析。发现起始材料 3-氨基-1H-1,2,4-三唑在溶液中以三种形式的互变异构混合物（图形摘要）存在，而在固态（13C 和 15N CPMAS 数据）中可能存在互变异构质子位于氮原子上，传统上标记为 N-2（图形摘要，2N H 结构）。所有研究的源自水杨醛的席夫碱都以互变异构平衡混合物的形式存在于两相中，其中烯醇亚胺形式是主导结构。这些平衡的位置仅非常轻微地取决于苯酚环中的取代基。通常，与 DMSO 溶液相比，固态中酮胺形式的贡献更高。

  DOI：

  10.1016/j.molstruc.2019.02.027

文献信息

• Synthesis, β-Glucuronidase Inhibition, and Molecular Docking Studies of 1,2,4-Triazole Hydrazones
  作者：Waqas Jamil、Darshana Kumari、Muhammad Taha、Muhammad Naseem Khan、Mohd Syukri Baharudin、Muhammad Ali、M. Kanwal、Muhammad Saleem Lashari、Khalid Muhammad Khan

  DOI：10.1007/s13738-018-1433-9

  日期：2018.11

  A series of 1,2,4-triazole hydrazones 1–25 has been synthesized and characterized using different spectroscopic techniques including FT-IR, 1H-NMR, and ESI MS spectrometry. The synthetic derivatives were evaluated for their β-glucuronidase enzyme inhibition properties. Among them, 17 compounds demonstrated potential inhibitory activity towards β-glucuronidase with IC50 values ranging between 2.50 and 53.70 µM. Compounds 1 having IC50 = 2.50 ± 0.01 µM was found to be the most active compound of the series and showed remarkable activity and found to be far more potent than the standard d-saccharic acid 1,4-lactone (IC50 = 48.4 ± 1.25 µM). Furthermore, the possible binding interaction of active compounds was explored by in silico studies. These compounds can be used for anti-diabetic drug development process.

  一系列1,2,4-三氮唑酰肼1至25已通过包括FT-IR、1H-NMR和ESI MS光谱在内的不同光谱技术合成并表征。这些合成衍生物被评估了其β-葡萄糖醛酸酶抑制特性。其中，17种化合物显示出对β-葡萄糖醛酸酶的潜在抑制活性，IC50值介于2.50至53.70 µM之间。化合物1的IC50 = 2.50 ± 0.01 µM被发现是该系列中最具活性的化合物，并显示出显著的活性，远比标准物质d-糖酸1,4-内酯（IC50 = 48.4 ± 1.25 µM）更强。此外，通过计算机模拟研究探索了活性化合物可能的结合交互作用。这些化合物可用于抗糖尿病药物的开发过程。
• A facile sonochemical protocol for synthesis of 3-amino- and 4-amino-1,2,4-triazole derived Schiff bases as potential antibacterial agents
  作者：Aeysha Sultan、Mian Habib Ur Rehman、Noreen Sajjad、Ali Irfan、Irfan Ullah、Muhammad Mustaqeem、Muhammad Saleem、Syeda Laila Rubab、Muhammad Rafiq、Muhammad Khalid、Katarzyna Kotwica-Mojzych、Mariusz Mojzych

  DOI：10.1371/journal.pone.0229891

  日期：——

  A facile method has been developed for the synthesis of Schiff bases derived from substituted and unsubstituted 3-amino- and 4-amino-1,2,4-triazoles. Condensation of the aminotrizoles with a variety of aromatic aldehydes afforded desired Schiff bases in excellent yields in 3-5 minutes of exposure to ultra-sound. The synthesized compounds were characterized by means of IR, 1HNMR and Mass spectrometry

  已经开发出一种简便的方法用于合成衍生自取代和未取代的3-氨基-和4-氨基-1,2,4-三唑的席夫碱。氨基三唑与各种芳香醛的缩合在超声波照射 3-5 分钟内以优异的产率提供了所需的席夫碱。通过IR、1HNMR和质谱对合成的化合物进行了表征。还筛选了合成的化合物对革兰氏阴性菌（大肠杆菌、宋内氏志贺氏菌、铜绿假单胞菌和伤寒沙门氏菌）和两种革兰氏阳性菌（金黄色葡萄球菌和枯草芽孢杆菌）菌株的抗菌潜力。
• Antiglycation Activity of Triazole Schiff’s Bases Against Fructosemediated Glycation: In Vitro and In Silico Study
  作者：Muniza Shaikh、Salman Siddiqui、Humaira Zafar、Uzma Naqeeb、Fakiha Subzwari、Rehan Imad、Khalid M. Khan、Muhammad I. Choudhary

  DOI：10.2174/1573406415666190212105718

  日期：2020.5.20

  Objectives: Two classes of previously synthesized traizole Schiff’s bases (4H-1,2,4-triazole-4- Schiff’s bases 1-14, and 4H-1,2,4-triazole-3-Schiff’s bases 15-23) were evaluated for their in vitro antiglycation activity. Methods: In vitro fructose-mediated human serum albumin (HSA) glycation assay was employed to assess the antiglycation activity of triazole Schiff’s bases. The active compounds were subjected

  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，
• Synthesis and Antifungal Activities of Some New 5,7-Disubstituted[1,2,4]Triazolo[1,5-<i>a</i>]Pyrimidin-6-one Derivatives
  作者：Susanta Kumar Borthakur、Sukanya Borthakur、Debarshi Goswami、Paran Boruah、Pabitra Kumar Kalita

  DOI：10.1002/jhet.2479

  日期：2016.11

  Synthesis of a new series of [1,2,4]triazolo[1,5‐a]pyrimidin‐6‐one by [4 + 2]cycloaddition reaction of 3‐benzylidineamino[1,2,4]triazole with monophenyl ketene and diphenyl ketene generated in situ from phenylacetyl chloride and diphenylacetyl chloride in the presence of triethylamine is described. The newly synthesized compounds were also tested for antifungal activities against Rhizoctonia solani

  通过3-苄基氨基[1,2,4]三唑与单苯基乙烯酮和[3]的[4 + 2]环加成反应合成一系列新的[1,2,4]三唑[1,5 - a ]嘧啶-6-one描述了在三乙胺存在下由苯基乙酰氯和二苯基乙酰氯原位生成的二苯基乙烯酮。还测试了新合成的化合物对茄根霉和木霉的抗真菌活性。
• 1H NMR, 13C NMR and mass spectral studies of some Schiff bases derived from 3-amino-1,2,4-triazole
  作者：Y.M. Issa、H.B. Hassib、H.E. Abdelaal

  DOI：10.1016/j.saa.2009.08.042

  日期：2009.11

  support for the results reached from 1H NMR studies. The mass spectral results are taken as a tool to confirm the structure of the investigated compounds. The base peak (100%), mostly the M-1 peak, indicates the facile loss of hydrogen radical. The fragmentation pattern of the unsubstituted Schiff base is taken as the general scheme. Differences in the other schemes result from the effect of the electronegativity

  制备衍生自3-氨基-1,2,4-三唑和不同取代的芳族醛的杂环席夫碱，并进行1 H NMR，13 C NMR和质谱分析。DMSO中的1 H NMR光谱在9.35–8.90 ppm区域内显示出尖锐的单峰，与偶氮甲碱质子相对应。该信号的位置在很大程度上取决于苯并部分的取代基的性质。可以看出，三唑环（5 C）芳香质子信号的形状，位置和积分值明显受到交换速率，弛豫时间，溶液浓度以及所用溶剂的影响。13C NMR被认为是1 H NMR研究结果的重要依据。质谱结果被用作确认所研究化合物结构的工具。基本峰（100％），主要是M-1峰，表明氢自由基的易失性。将未取代的席夫碱的片段化模式作为一般方案。其他方案的差异是由于芳环上连接的取代基的电负性影响所致。

表征谱图