4-amino-5-ethyl-2,4-dihydro-[1,2,4]triazol-3-one | 4379-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-amino-5-ethyl-2,4-dihydro-[1,2,4]triazol-3-one
• 英文别名: 3-ethyl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-one；4-amino-3-ethyl-1H-1,2,4-triazol-5-one
• CAS: 4379-93-5
• 化学式: C₄H₈N₄O
• 分子量: 128.134
• InChiKey: ZXGTZAGVVNTWAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.7
• 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：

  柠康酸酐 、 4-amino-5-ethyl-2,4-dihydro-[1,2,4]triazol-3-one 反应 1.5h， 以76%的产率得到
  参考文献：
  名称：

  Ikizler; Bahceci; Ikizler, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 2, p. 137 - 140

  摘要：

  DOI：
• 作为产物：
  描述：

  Ethylpropionatcarbethoxyhydrazon 在 一水合肼 作用下， 以 水 为溶剂， 反应 0.05h， 生成 4-amino-5-ethyl-2,4-dihydro-[1,2,4]triazol-3-one
  参考文献：
  名称：

  微波和常规方法合成含有靛红作为潜在抗菌剂和抗真菌剂的新型三唑化合物

  摘要：

  微波辐射已被用于加速靛红 (1a) 和 5-硝基靛红 (1b) 转化为它们的希夫碱 3-[5'-芳基(烷基)-2',4'-二氢-1',2', 4'-triazol-3'-on-4'-yl]iminoisatin (3a–g) 和 3-[5'-aryl(烷基)-2',4'-dihydro-1',2',4'- triazol-3'-on-4'-yl]imino-5-nitroisatin (4a–g) 分别。反应采用微波诱导技术，与传统加热相比，大大缩短了反应时间，提高了产率。新合成的碱基对所测试的标准细菌和真菌生物显示出中等的抗菌活性

  DOI：

  10.3184/174751911x13043524455143

文献信息

• Synthesis of new derivatives of 4-amino-2,4-dihydro-1,2,4-triazol-3-one as potential antibacterial agents
  作者：Frédérique Malbec、René Milcent、Patrick Vicart、Anne Marie Bure

  DOI：10.1002/jhet.5570210641

  日期：1984.11

  characterised by their sharp melting points, elemental analysis, ir and 1H nmr spectra. These new derivatives of 5-nitro-2-furaldehyde were screened for their antibacterial activities. Most of the compounds showed good activity against one test organism, Staphylococcus aureus. For a few compounds, C.M.I. ranged from 4 to 8 μg/ml (higher results than nitrofurantoin).

  三十个新的2-取代的-4-氨基-5-烷基或芳基-2,4-二氢-1,2,4-三唑-3-酮和十个2-取代的-5-烷基或芳基-4-（5-合成了硝基-2-糠基亚氨基）氨基-2,4-二氢-1,2,4-三唑-3-酮，并通过其尖锐的熔点，元素分析，ir和1 H nmr光谱对其进行了表征。筛选了5-硝基-2-呋喃甲醛的这些新衍生物的抗菌活性。大多数化合物对一种测试生物金黄色葡萄球菌显示出良好的活性。对于一些化合物，CMI范围为4至8μg/ ml（比呋喃妥因更高的结果）。
• Synthesis and in vitro antioxidant and antimicrobial activities of novel 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones, and their N-acetyl, N-Mannich base derivatives
  作者：Sevda Manap

  DOI：10.1007/s13738-021-02386-7

  日期：2022.4

  The reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1) with 3-methoxy-4-(2-furylcarbonyloxy)-benzaldehyde (2) formed 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones (3). Moreover, their five N-acetyl derivatives were synthesized. Besides, 1-(morpholine-4-yl-methyl)-3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones (5)/1-(4-methylpiperazin-1-yl-methyl)-3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones (6)/1-(piperidine-4-carboxyamide-1-yl-methyl)-3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones (7)/N,N′-bis-3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylideneamino]-4,5-dihydro-1H-1,2,4-triazol-5-on-1-yl-methyl}-piperazines (8) were obtained by Mannich reaction between compounds 3 and morpholine/N-methylpiperazine/piperidine-4-carboxyamide/piperazine in the presence of formaldehyde. The newly obtained thirty-four compounds were characterized from IR, 1H NMR, 13C NMR, and MS spectral data. Also, these compounds were evaluated for their in vitro antioxidant activity. Furthermore, in vitro antibacterial activity of the compounds was screened against six bacteria.

  3- 烷基（芳基）-4-氨基-4,5-二氢-1H-1,2,4-三唑-5-酮 (1) 与 3-甲氧基-4-（2-呋喃甲酰氧基）-苯甲醛 (2) 反应生成了 3-烷基（芳基）-4-[3-甲氧基-4-（2-呋喃甲酰氧基）-亚苄基氨基]-4,5-二氢-1H-1,2,4-三唑-5-酮 (3)。此外，还合成了它们的五个 N-乙酰基衍生物。此外，还合成了 1-(吗啉-4-基-甲基)-3-烷基(芳基)-4-[3-甲氧基-4-(2-呋喃甲酰氧基)-亚苄基氨基]-4,5-二氢-1H-1,2,4-三唑-5-酮 (5)/1-(4- 甲基哌嗪-1-基-甲基)-3-烷基(芳基)-4-[3-甲氧基-4-(2-呋喃甲酰氧基)-亚苄基氨基]-4,5-二氢-1H-1,2,4-三唑-5-酮 (6)、5-dihydro-1H-1,2,4-triazol-5-ones (7)/N,N′-bis-3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylideneamino]-4,5-dihydro-1H-1,2,化合物 3 与吗啉/N-甲基哌嗪/哌啶-4-羧酰胺/哌嗪在甲醛存在下发生曼尼希反应，得到了 4,5-二氢-1H-1,2,4-三唑-5-on-1-基-甲基}-哌嗪（8）。根据红外光谱、1H NMR、13C NMR 和 MS 光谱数据对新得到的 34 种化合物进行了表征。此外，还对这些化合物的体外抗氧化活性进行了评估。此外，还筛选了这些化合物对六种细菌的体外抗菌活性。
• Synthesis, design, and assessment of novel morpholine-derived Mannich bases as multifunctional agents for the potential enzyme inhibitory properties including docking study
  作者：Songül Boy、Fikret Türkan、Murat Beytur、Abdülmelik Aras、Onur Akyıldırım、Halide Sedef Karaman、Haydar Yüksek

  DOI：10.1016/j.bioorg.2020.104524

  日期：2021.2

  The synthesized Schiff Bases were reacted with formaldehyde and secondary amine such as 2,6-dimethylmorpholine to afford N-Mannich bases through the Mannich reaction. 3-Substitued-4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (4) were treated with 2,6-dimethylmorpholine in the presence of formaldehyde to synthesize eight new 1-(2,6-dimethylmorpholino-4-yl-methyl)-3-substitued-4-

  合成的席夫碱与甲醛和仲胺如2,6-二甲基吗啉反应，通过曼尼希反应得到N-曼尼希碱。3-取代的-4-（4- hydroxybenzylidenamino）-4,5-二氢-1- ħ -1,2,4-三唑-5-酮（4）在甲醛存在下，以合成用2,6-二甲基吗啉处理八种新的 1-(2,6-dimethylmorpholino-4-yl-methyl)-3-substitued-4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones ( 4a-h)。合成的8个新化合物的结构使用IR、1 H NMR、13C NMR和HR-MS光谱方法。合成化合物对乙酰胆碱酯酶 (AChE)、丁酰胆碱酯酶 (BChE) 和谷胱甘肽 S-转移酶 (GST) 的抑制活性测定，AChE 的 Ki 值范围为 25.23-42.19 µM，BChE.8 的 Ki
• Synthesis, Spectroscopic Analysis, and <i>in Vitro/in Silico</i> Biological Studies of Novel Piperidine Derivatives Heterocyclic Schiff‐Mannich Base Compounds
  作者：Songül Boy、Abdülmelik Aras、Fikret Türkan、Onur Akyıldırım、Murat Beytur、Halide Sedef Karaman、Sevda Manap、Haydar Yüksek

  DOI：10.1002/cbdv.202100433

  日期：2021.12

  to afford novel heterocyclic bases. 3-Substitued-4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (T) were treated with 4-piperidinecarboxyamide in the presence of formaldehyde to synthesize eight new 1-(4-piperidinecarboxyamide-1-yl-methyl)-3-substitued-4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (M1-8). The structure characterization of compounds was carried out

  在本研究中，通过处理 4-羟基苯甲醛（B )在乙酸介质中分别使用八种不同的 3-取代-4-氨基-4,5-二氢-1 H -1,2,4-三唑-5-酮 ( T1-8 )。合成的席夫碱( S )与甲醛和仲胺如4-哌啶甲酰胺反应得到新型杂环碱。3-取代-4-(4-羟基苄基氨基)-4,5-dihydro-1 H -1,2,4-triazol-5-ones ( T)在甲醛存在下用4-哌啶甲酰胺处理合成8个新的1-(4-哌啶甲酰胺-1-基-甲基)-3-取代-4-(4-羟基苄基氨基)-4,5-二氢-1H -1,2,4-triazol -5-ones ( M1-8 )。化合物的结构表征使用1 H-NMR、IR、HR-MS 和13 C-NMR 光谱方法进行。计算了新合成的化合物对乙酰胆碱酯酶 (AChE)、丁酰胆碱酯酶 (BChE) 和谷胱甘肽 S-转移酶 (GST) 酶的抑制特性。Ki 值的计算范围为 GST
• The Syntheses, Molecular Structures, Spectroscopic Properties (IR, Micro– Raman, NMR and UV–vis) and DFT Calculations of Antioxidant 3– alkyl–4–[3–methoxy–4–(4–methylbenzoxy)benzylidenamino]–4,5–dihydro– 1H–1,2,4–triazol–5–one Molecules
  作者：Halil Gokce、Semiha Bahceli、Onur Akyildirim、Haydar Yuksek、Ozlem Kol

  DOI：10.2174/15701786113109990001

  日期：2013.6.1

  The syntheses, antioxidant activities, acidity properties, experimental and theoretical investigations of vibrational spectra (FT–IR and micro–Raman), 13C and 1H NMR chemical shifts and electronic properties of 3–alkyl–4–[3– methoxy–4–(4–methylbenzoxy)benzylidenamino]–4,5–dihydro–1H–1,2,4–triazol–5–one (Me, Et and n–Pr) molecules have been presented for the first time. The new compounds were analyzed for their potential antioxidant activities in three different methods.The calculations of molecular structures, vibrational frequencies, 13C and 1H NMR chemical shifts and electronic absorption wavelengths of the title molecules were computed by using the DFT/B3LYP method with 6– 31G(d) basis set which was used to have the structural and spectroscopic data about the mentioned molecules in the ground state and the results calculated were compared with experimental values. Furthermore, gauge invariant atomic orbital (GIAO) 1H and 13C NMR chemical shifts in different solvents (gas phase, DMSO and cholorofom), UV–vis. TD– DFT calculations in ethanol solvent, the highest occupied molecular orbital (HOMO–1, HOMO), lowest unoccupied molecular orbital (LUMO, LUMO+1), molecular electrostatic potential map (MEP), atomic charges and thermodynamic properties of the title compounds have theoretically verified and simulated at the mentioned level. In addition, the calculated infrared intensities and Raman activities of the compounds under study have also been reported.

  首次介绍了 3-烷基-4-[3-甲氧基-4-(4-甲基苯氧基)亚苄基氨基]-4,5-二氢-1H-1,2,4-三唑-5-酮（Me、Et 和 n-Pr）分子的合成、抗氧化活性、酸性、振动光谱（傅立叶变换红外光谱和显微拉曼光谱）、13C 和 1H NMR 化学位移以及电子特性的实验和理论研究。利用 DFT/B3LYP 方法和 6- 31G(d) 基集计算了标题分子的分子结构、振动频率、13C 和 1H NMR 化学位移以及电子吸收波长，并将计算结果与实验值进行了比较。此外，在不同溶剂（气相、DMSO 和 Cholorofom）、紫外-可见光（UV-vis.在乙醇溶剂中进行的 TD- DFT 计算，对标题化合物的最高占位分子轨道（HOMO-1、HOMO）、最低未占位分子轨道（LUMO、LUMO+1）、分子静电位图（MEP）、原子电荷和热力学性质进行了理论验证和上述水平的模拟。此外，还报告了所研究化合物的计算红外强度和拉曼活性。