3-propyl-4-amino-4,5-dihydro-1,2,4-triazol-5-one | 75989-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-propyl-4-amino-4,5-dihydro-1,2,4-triazol-5-one
• 英文别名: 4-Amino-5-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one；4-amino-3-propyl-1H-1,2,4-triazol-5-one
• CAS: 75989-56-9
• 化学式: C₅H₁₀N₄O
• 分子量: 142.161
• InChiKey: YSORPAIURFODQD-UHFFFAOYSA-N

物化性质

• 熔点：
  145.5 °C(Solv: ethyl acetate (141-78-6))
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-propyl-4-amino-4,5-dihydro-1,2,4-triazol-5-one 在 sodium 、 一水合肼 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 14.0h， 生成 (4-Amino-5-oxo-3-propyl-4,5-dihydro-[1,2,4]triazol-1-yl)-acetic acid [1-phenyl-meth-(E)-ylidene]-hydrazide
  参考文献：
  名称：

  Synthesis and antimicrobial activities of some new 1-(5-phenylamino-[1,3,4]thiadiazol-2-yl)methyl-5-oxo-[1,2,4]triazole and 1-(4-phenyl-5-thioxo-[1,2,4]triazol-3-yl)methyl-5-oxo- [1,2,4]triazole derivatives

  摘要：

  Acetic acid ethyl esters containing 5-oxo-[1,2,4]triazole ring (2) were synthesized by the condensation of compounds 1a-f with ethyl bromoacetate in basic media. The reaction of compounds 2a-f with hydrazine hydrate led to the formation of acid hydrazides (3a-f). The treatment of compounds 3 with two divers aromatic aldehydes resulted in the formation of arylidene hydrazides as cis-tralls conformers (4a,c,e,f, 5a,e,f). The thiosemicarbazide derivatives (6a,c,d,f) were afforded by the reaction of corresponding compounds 3 with phenylisothiocyanate. The treatment of compounds 6a,c,d,f with sulfuric acidic caused the conversion of side-chain of compounds 6a,c,d,f into 1,3,4-thiadiazol ring; thus, compounds 7a,c,d,f were obtained. On the other hand, the cyclization of compounds 6a,c,d,f in the presence of 2 N NaOH resulted in the formation of compounds 8a,c,d,f containing two [1,2,4]triazole rings which are linked to each other via it methylene bridge. Compounds 4a, f, 5a, 7a, d, f, 8a and d have shown antimicrobial activity against one or more microorganism, but no antifungal activity has been observed against yeast like fungi. Also inhibitory effect on mycelial growth by compounds 4e, 7d and 8f hits been observed. Compounds 4c and 5f were found to possess antitumor active towards breast cancer. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.06.007
• 作为产物：
  描述：

  Ethylbutyratcarbethoxyhydrazon 在 肼 作用下， 以 水 为溶剂， 生成 3-propyl-4-amino-4,5-dihydro-1,2,4-triazol-5-one
  参考文献：
  名称：

  一些新型4,5-二氢-1H-1,2,4-三唑-5-酮衍生物的合成、体外抗菌和抗氧化活性

  摘要：

  合成了一系列衍生自 4,5-dihydro-1H-1,2,4-triazol-5-one 的化合物，并通过光谱数据表征。通过三种不同的方法分析了 12 种新化合物的潜在体外抗氧化活性。化合物4f显示出最佳的铁结合活性。此外，化合物 4 在非水溶剂中用四丁基氢氧化铵进行电位滴定。该系列的 RP-HPLC 容量因子 (k') 也在 C18 柱上测定，甲醇/水作为流动相。log k' 与流动相中甲醇百分比之间的相关性用于确定这些化合物的 log kw 值。还筛选了这些化合物对细菌和酵母菌的抗微生物活性。

  DOI：

  10.1002/ardp.201300048

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。
• 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。
• Synthesis,<i>In Vitro</i>Antimicrobial and Antioxidant Activities of Some New 4,5-Dihydro-1<i>H</i>-1,2,4-triazol-5-one Derivatives
  作者：Haydar Yüksek、Onur Akyıldırım、Mehmet L. Yola、Özlem Gürsoy-Kol、Mustafa Çelebier、Didem Kart

  DOI：10.1002/ardp.201300048

  日期：2013.6

  series of compounds derived from 4,5‐dihydro‐1H‐1,2,4‐triazol‐5‐one were synthesized and characterized by spectral data. The 12 new compounds were analyzed for their potential in vitro antioxidant activities by three different methods. Compound 4f showed the best activity for the iron binding. In addition, the compounds 4 were titrated potentiometrically with tetrabutylammonium hydroxide in non‐aqueous

  合成了一系列衍生自 4,5-dihydro-1H-1,2,4-triazol-5-one 的化合物，并通过光谱数据表征。通过三种不同的方法分析了 12 种新化合物的潜在体外抗氧化活性。化合物4f显示出最佳的铁结合活性。此外，化合物 4 在非水溶剂中用四丁基氢氧化铵进行电位滴定。该系列的 RP-HPLC 容量因子 (k') 也在 C18 柱上测定，甲醇/水作为流动相。log k' 与流动相中甲醇百分比之间的相关性用于确定这些化合物的 log kw 值。还筛选了这些化合物对细菌和酵母菌的抗微生物活性。
• Synthesis, in vitro antioxidant activity, and physicochemical properties of novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives
  作者：Haydar Yüksek、Ebru Koca、Özlem Gürsoy-Kol、Onur Akyıldırım、Mustafa Çelebier

  DOI：10.1016/j.molliq.2015.02.038

  日期：2015.6

  characterized using IR, 1H NMR, 13C NMR, and UV spectral data. In addition, the synthesized compounds were analyzed for their potential in vitro antioxidant activities, including reducing power, free radical scavenging and metal chelating activity. These antioxidant activities were compared to those from standard antioxidants, such as EDTA, BHA, BHT and α-tocopherol. Moreover, compounds 4 were titrated potentiometrically

  在这项研究中，八个新的3-烷基（芳基）-4- [4-（4-甲基苯甲酰）苄叉氨基] -4,5-二氢-1 H -1,2,4-三唑-5-酮（4）化合物通过3-烷基（芳基）-4-氨基-4,5-二氢-1 H -1,2,4-三唑-5-酮（3）与4-（4-甲基苯并）苯甲醛（1）。使用IR，1 H NMR，13对8种化合物进行了表征1 H NMR和UV光谱数据。此外，分析了合成化合物的潜在体外抗氧化活性，包括还原能力，自由基清除作用和金属螯合活性。将这些抗氧化剂活性与标准抗氧化剂（例如EDTA，BHA，BHT和α-生育酚）的抗氧化剂活性进行了比较。此外，在四种非水溶剂（异丙醇，叔丁醇，丙酮和N，N-二甲基甲酰胺）中，用氢氧化四丁铵电位滴定化合物4。因此，半中和电位值和相应的p K a在所有情况下均确定值。另外，使用HPLC研究了合成化合物的亲脂性。使用Coats–Redfern和Horowitz–Metz