N-(furan-2-ylmethylene)-1H-1,2,4-triazole-3-amine | 89975-90-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(furan-2-ylmethylene)-1H-1,2,4-triazole-3-amine
• 英文别名: furan-2-ylmethylene-(1H-[1,2,4]triazol-3-yl)amine；furan-2-ylmethylene-(1H-1,2,4-triazol-3-yl)amine；furfurylidene-(1H-[1,2,4]triazol-3-yl)-amine；Furfuryliden-(1H-[1,2,4]triazol-3-yl)-amin；N-(furan-2-yl-methylene)-1h-1,2,4-triazole-3-amine；1-(furan-2-yl)-N-(1H-1,2,4-triazol-5-yl)methanimine
• CAS: 89975-90-6
• 化学式: C₇H₆N₄O
• 分子量: 162.151
• InChiKey: VNRKMYIZSYYQSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 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：
  67.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cobalt(II) diacetate tetrahydrate 、 N-(furan-2-ylmethylene)-1H-1,2,4-triazole-3-amine 以 甲醇 为溶剂， 反应 0.08h， 以74.91%的产率得到
  参考文献：
  名称：

  Synthesis of some triazole Schiff base derivatives and their metal complexes under Microwave irradiation and evaluation of their corrosion inhibition and biological activity

  摘要：

  TWO triazole Schiff base derivatives N-(furan-2-ylmethylene)-1H-1,2,4-triazole-3-amine (FTA), N-(thiophene-2-ylmethylene)-1H-1,2,4-triazole-3-amine (TTA) and their metal complexes Co(II), Ni(II), Cu(II) and Zn(II) were synthesized under microwave irradiation. The structure of these compounds has been investigated by using elemental analysis, FT-IR, UV-Vis spectrometric methods, magnetic susceptibility, mass spectra, NMR, ESR and thermal studies. The antimicrobial activities of the prepared ligands and their respective Zn (II) complexes were studied against the bacterial (positive and negative) grams and fungal strains. The inhibitive characteristics of Schiff base ligands on C-steel corrosion in hydrochloric acid were studied using weight loss measurements. The prepared Schiff base derivatives show high inhibition efficiency and their adsorption surface was found to obey Langmuir model. The data also revealed that FTA is less than TTA in terms of inhibiting efficiency.

  DOI：

  10.21608/ejchem.2019.10834.1699
• 作为产物：
  描述：

  糠醛 、 3-氨基-1,2,4-三氮唑 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.07h， 以79%的产率得到N-(furan-2-ylmethylene)-1H-1,2,4-triazole-3-amine
  参考文献：
  名称：

  常规和微波辅助合成某些席夫碱及其作为抗菌剂的潜力的比较研究

  摘要：

  一系列的席夫碱（化合物1 - 10）通过穿过两个缩合杂环/芳族醛与杂环/芳族胺的合成，现有的方法和微波辅助合成。通过IR光谱，质谱，1 H NMR和元素分析确认化合物。通过区域抑制法测定了这些化合物对所选革兰氏阳性，革兰氏阴性细菌和某些真菌菌株的抗菌活性。还确定了每种化合物的最小抑菌浓度（MIC）。通过微波辅助合成，反应时间大大减少。化合物2的MIC低至50μg/ ml （针对大肠杆菌，黑曲霉和产黄青霉（Penicillium chrysogenum）和10（对抗枯草芽孢杆菌）。该研究通过有效和简单的反应以及温和的反应条件提出了一系列潜在的抗菌剂，从而提供了一种绿色化学方法。

  DOI：

  10.1007/s00044-011-9592-6

文献信息

• Comparative study of conventional and microwave-assisted synthesis of some Schiff bases and their potential as antimicrobial agents
  作者：Vikas Pandey、Viney Chawla、Shailendra K. Saraf

  DOI：10.1007/s00044-011-9592-6

  日期：2012.6

  A series of Schiff bases (compounds 1–10) were synthesized by condensing heterocyclic/aromatic aldehydes with heterocyclic/aromatic amines through both, conventional method and microwave-assisted synthesis. The compounds were confirmed by means of IR spectroscopy, Mass spectrometry, 1H NMR and elemental analyses. The compounds were assayed for antibacterial activity against selected strains of Gram

  一系列的席夫碱（化合物1 - 10）通过穿过两个缩合杂环/芳族醛与杂环/芳族胺的合成，现有的方法和微波辅助合成。通过IR光谱，质谱，1 H NMR和元素分析确认化合物。通过区域抑制法测定了这些化合物对所选革兰氏阳性，革兰氏阴性细菌和某些真菌菌株的抗菌活性。还确定了每种化合物的最小抑菌浓度（MIC）。通过微波辅助合成，反应时间大大减少。化合物2的MIC低至50μg/ ml （针对大肠杆菌，黑曲霉和产黄青霉（Penicillium chrysogenum）和10（对抗枯草芽孢杆菌）。该研究通过有效和简单的反应以及温和的反应条件提出了一系列潜在的抗菌剂，从而提供了一种绿色化学方法。
• 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。
• 3-furfurylidene-aminmo-1, 2, 4-triazole and process for producing same
  申请人：BAYER AG

  公开号：US02870144A1

  公开（公告）日：1959-01-20

  The invention comprises 3-furfurylidineamino-1:2:4-triazole and the preparation thereof by reacting together equimolecular quantities of furfural and 3-amino-1:2:4-triazole, preferably at a temperature of 40 DEG to 50 DEG C. and in an inert organic solvent such as methanol or ethanol.ALSO:A plant growth control composition for use in defoliating cotton plants comprises 3-furfurylidine-amino-1 : 2 : 4-triozole in admixture with an inert solid or liquid carrier and, if desired, wetting agents, emulsifiers, dispersing agents, agents promoting penetration, fertilizers and/or other herbicides. An exemplified composition comprises a 0,1 to 0,5% by weight aqueous solution of active ingredient containing ortho-benzyl-hydroxydiphenyl polyglycol ether as an emulsifying agent.ALSO:A plant growth control composition for use in defoliating cotton plants comprises 3-furfurylidine-amino-1 : 2 : 4-triazole in admixture with an inert solid or liquid carrier and, if desired, wetting agents, emulsifiers, dispersing agents, agents promoting penetration, fertilizers and/or other herbicides. An exemplified composition comprises a 0.1 to 0.5% by weight aqueous solution of active ingredient containing ortho - benzyl - hydroxy - diphenylpolyglycol ether as an emulsifying agent.

  该发明包括3-呋喃基亚胺基-1:2:4-三唑及其制备方法，该方法是将等分子量的呋喃醛和3-氨基-1:2:4-三唑在惰性有机溶剂（如甲醇或乙醇）中反应，最好在40℃至50℃的温度下进行。此外，一种用于除叶棉花植株的植物生长控制组合物包括3-呋喃基亚胺基-1:2:4-三唑与惰性固体或液体载体混合，并且，如果需要，还包括润湿剂、乳化剂、分散剂、促进渗透剂、肥料和/或其他除草剂。一种示例组合物包括0.1至0.5重量％的活性成分水溶液，其中含有邻苯基-羟基-二苯基聚醚作为乳化剂。
• Bast,K. et al., Chemische Berichte, 1972, vol. 105, p. 2825 - 2840
  作者：Bast,K. et al.

  DOI：——

  日期：——
• Synthesis of some triazole Schiff base derivatives and their metal complexes under Microwave irradiation and evaluation of their corrosion inhibition and biological activity
  作者：Ali Hassan、Bassem Heakal、Ahmed Younis、Mahmoud Bedair、zaghloul El - Billy、Moataz Mohamed

  DOI：10.21608/ejchem.2019.10834.1699

  日期：2019.4.8

  TWO triazole Schiff base derivatives N-(furan-2-ylmethylene)-1H-1,2,4-triazole-3-amine (FTA), N-(thiophene-2-ylmethylene)-1H-1,2,4-triazole-3-amine (TTA) and their metal complexes Co(II), Ni(II), Cu(II) and Zn(II) were synthesized under microwave irradiation. The structure of these compounds has been investigated by using elemental analysis, FT-IR, UV-Vis spectrometric methods, magnetic susceptibility, mass spectra, NMR, ESR and thermal studies. The antimicrobial activities of the prepared ligands and their respective Zn (II) complexes were studied against the bacterial (positive and negative) grams and fungal strains. The inhibitive characteristics of Schiff base ligands on C-steel corrosion in hydrochloric acid were studied using weight loss measurements. The prepared Schiff base derivatives show high inhibition efficiency and their adsorption surface was found to obey Langmuir model. The data also revealed that FTA is less than TTA in terms of inhibiting efficiency.