Synthesis, Antibacterial, Antiurease, and Antioxidant Activities of Some New 1,2,4-Triazole Schiff Base and Amine Derivatives

Sökmen, Bahar Bilgin; Gümrükçüoğlu, Nurhan; Uğraş, Serpil; Şahin, Hüseyin; Sagkal, Yasemin; Uğraş, Halil İbrahim

doi:10.1007/s12010-014-1307-2

Cited by 17 publications

(4 citation statements)

References 27 publications

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“…The strong infrared absorption at 1633 cm -1 , that corresponds to (C=N) of the aminoguanidine bicarbonate, has split up in two new absorptions in the range of 1705 to 1575 cm -1 in the spectra of the triazoles mta, pta and mpta. The third additional infrared absorption for the mpta compound at 1579 cm -1 was assigned to the (C=N) of the imine group outside of the triazole ring, similar to other Schiff bases derivatives (Sokmen et al, 2015;Tyagi et al, 2017;Wajda-Hermanowicz et al, 2016).…”

Section: Infrared Spectroscopymentioning

confidence: 68%

Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate

et al. 2022

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The condensation reaction between aminoguanidine bicarbonate with carboxylic acids led to the formation of 3-methyl-1H-1,2,4-triazole-5-amine (mta), 3-methyl-1H-1,2,4l4-triazole-5-amine acetate (Hmta) and 3-phenyl-1H-1,2,4-triazole-5-amine (pta). The compound N-(3-methyl-1H-1,2,4-triazole-5-yl)propan-2-imine (mpta) was obtained by reacting the mta with acetone, upon an attempt of purifying mta in this solvent. The excess of acetic acid obtained the Hmta during the preparation of mta. These compounds were characterised by infrared and multinuclear NMR (1H and 13C) spectroscopy, microanalysis, and melting point. To investigate the formation of possible tautomeric conformations of mta, pta and mpta in solution, a theoretical approach was used to calculate the chemical shifts of carbon 13, based on the values of magnetic shielding tensor (NMR) by MPn and DFT methods. The biological assay of the triazoles mta, pta and mpta against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Salmonella typhimurium showed no activity at the highest concentration used in the experiment.

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Section: Infrared Spectroscopymentioning

confidence: 68%

Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate

et al. 2022

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“…Thus, the search for new promising molecules among 1,2,4-triazole substitutes which can be used as object to create potential antimicrobial or antifungal agents remains relevant, has theoretical and practical importance [5].…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial activity of new 5-(furan-2-yl)-4-amino-1,2,4-triazole-3-thiol derivatives

Danilchenko

Парченко

2017

ZMJ

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The aim of this research was to investigate the antimicrobial activity of some new 5-(furan-2-yl)-4-amino-1,2,4-triazole-3-thiol substituents and in some cases to trace the relationship between activity of compounds and their structure.Materials and methods. Antimicrobial activity of new 5-(furan-2-yl)-4-amino-1,2,4-triazole-3-thiol derivatives was studied by the method of serial dilutions. The primary antimicrobial activity screening tests of some 5-(furan-2-yl)-4-amino-1,2,4-triazole-3-thiol derivatives have been conducted on standard test cultures of both gram-positive and gram-negative bacteria that belong to clinically significant group of infectious agents with different morphological properties. Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853 were taken as the set of standard test strains.Results and discussion. The most sensitive strain was a strain of S. aureus ATCC 25923. Extension of alkyl substituents by the Sulfur atom does not lead to gradual changes in activity but the introduction of pentyl radical increases the activity of a molecule in two times. The transition from the S-alkyl derivatives of 5-(furan-2-yl)-4-amino-1,2,4-triazole-3-thiol to 2-((5-(furan-2-yl)-4-amino-1,2,4-triazole-3-yl)-thio)acetic acid esters doesn't lead to radical changes of antimicrobial activity and is not drawn. But the introduction of isopropyl and isobutyl radicals in the ester structure of these molecules leads to a sharp increase in activity towards S. aureus ATCC 25923. Conclusions.We have explored antimicrobial activity of new 5-(furan-2-yl)-4-amino-1,2,4-triazole-3-thiol alkyl derivatives and 2-((5-(furan-2-yl)-4-amino-1,2,4-triazole-3-yl)thio)acetic acid esters. It was found that all ten compounds exhibit moderate activity. Some influence of studied substituents on the antimicrobial activity results was also found.Протимікробна активність нових похідних 5-(фуран-2-іл)-4-аміно-1,2,4-тріазол-3-тіолівМета роботи -дослідити протимікробну активність ряду нових похідних 5-(фуран-2-іл)-4-аміно-1,2,4-тріазол-3-тіолів, у деяких випадках простежити взаємозв'язок між активністю сполук та їхньою будовою.Матеріали та методи. Протимікробну активність нових похідних 5-(фуран-2-іл)-4-аміно-1,2,4-тріазол-3-тіолів вивчали за методом серійних розведень. З вихідної концентрації нових синтезованих сполук 1 мг/мл готували ряд двократних серійних розведень у бульйоні Мюллер-Хінтона в об'ємі 1 мл. Первинні скринінгові випробування протимікробної активності ряду похідних 5-(фуран-2-іл)-4-аміно-1,2,4-тріазол-3-тіолів проводили на еталонних тест-культурах як грампозитивних, так і грамнегативних бактерій, що належать до різних за морфофізіологічними властивостями клінічно значущих груп збудників інфекційних захворювань. Як набір стандартних тест-штамів взято Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853.Результати. Здійснюючи порівняльний аналіз результатів наявності протимікробної дії нових алкілпохідних 5-(фуран-2-іл)-4-аміно-1,2,4-тріазол-...

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“…The 1,2,4-triazole compounds represent an important nitro-containing heterocycles with extensively bioactivities [7][8][9][10], such as anti-inflammatory activity [11], anticancer OPEN ACCESS activity [12], anti-oxidation activity [13,14], herbicidal activity [15],antifungal activity [16,17], antiurease activity [18], antidepressant activity [19] and so on. Moreover, 1,2,4-triazole substructure was found in many commercial pesticide or drugs, especially in antifungal medicines ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Synthesis and Antifungal Activity of Some Novel Thioethers Containing 1,2,4-Triazole Moiety

Liu

Shi

et al. 2015

Applied Sciences

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A series of novel thioether derivatives containing 1,2,4-triazole moiety were designed and synthesized from 4-chlorophenol and ethyl 2-chloroacetate as starting materials by multi-step reactions under microwave irradiation, and their structures were characterized by 1 H-NMR, MS and elemental analysis. The antifungal activity of title compounds was determined. The results indicated that some of title compounds exhibited moderate antifungal activity.

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Synthesis, Antibacterial, Antiurease, and Antioxidant Activities of Some New 1,2,4-Triazole Schiff Base and Amine Derivatives

Cited by 17 publications

References 27 publications

Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate

Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate

Antimicrobial activity of new 5-(furan-2-yl)-4-amino-1,2,4-triazole-3-thiol derivatives

Microwave-Assisted Synthesis and Antifungal Activity of Some Novel Thioethers Containing 1,2,4-Triazole Moiety

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