Synthesis and Antimicrobial Activity of Functional Derivatives of thiazolo[ 2,3-c][1,2,4]triazoles

Slivka, Mikhailo; Fizer, Maksym; Mariychuk, Ruslan; Ostafin, Marek; Moyzesh, Olexander; Koval, Galyna; Kamoshenkova, Oksana Holovko-; Rusyn, Ivan; Lendel, Vasy l

doi:10.2174/1570180819666220110145659

LDDD

2022

DOI: 10.2174/1570180819666220110145659

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Synthesis and Antimicrobial Activity of Functional Derivatives of thiazolo[ 2,3-c][1,2,4]triazoles

Mikhailo Slivka

Maksym Fizer

Ruslan Mariychuk

et al.

Abstract: Background: Condensed triazoles are a well-known class of heterocyclic compounds due to a wide range of biological activity. The study is dedicated to the evaluation of the antimicrobial potential of new functional derivatives of thiazolo[2,3-c][1,2,4]triazoles. Methods: Effective, easy-to-implement and low-cost routes to the production of title compounds via electrophilic intramolecular heterocyclization are reported. Bactericidal and fungicidal activities against Gram-positive and Gram-negative bacteria, a… Show more

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Cited by 2 publications

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Aryltellurochlorination of 5-Aryl(heteryl)substituted N-Allyl-1,2,4-Triazole-3-Thione Derivatives

Onisko

2023

Ukr. Chem. Journ.

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Condensed heterocycles based on 1,2,4-triazole have a wide range of biological activity. The introduction of a pharmacophore fragment of an aryl tertiary residue into their composition can significantly increase the bioactivity of the obtained compounds. Therefore, the synthesis of condensed derivatives of symmetrical 1,2,4-triazole with aryltellurium fragment is an urgent task. One of the most convenient and effective methods for introducing an aryltellurium fragment into such systems is the method of electrophilic intramolecular cyclisation of alkenyl derivatives of azaheterocycles. The aim of this work was to determine the effect of the nature of the substituent at position five of the initial N-allyl derivatives of 1,2,4-triazol-3-thione on the regioselectivity of electrophilic heterocyclization with p-methoxyphenyltellurium trichloride. The reaction of tellurium-induced heterocyclisation of N-allyl-substituted 1,2,4-triazole-3-thione with was carried out in acetic acid medium at room temperature under stirring for 12 hours. It was found that the reactions of 5-aryl(heteryl)substituted N-allyl derivatives of 1,2,4-triazole-3-thione with p-methoxyphenyltellurium trichloride lead to the formation of chlorides 6-((dichloro(4-methoxyphenyl)-λ4-tellanyl)methyl)-5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-1-ium chlorides with an exocyclic p-methoxyphenyltellurium fragment. The yield of the obtained thiazolotriazolium salts was 68-87%. It should be noted that the use of a double amount of electrophilic reagent did not lead to the formation of a thiazolotriazole complex with p-methoxyphenyltellurium trichloride, which was observed during the heterocyclisation of S-alkenyl derivatives of 1,2,4-triazole. Thus, the tellurium-induced cyclization of 5-substituted N-allyl derivatives of 1,2, 4-triazol-3-thione derivatives by p-methoxyphenyltellurium trichloride is regioselective with the formation of 6-((dichloro(4-methoxyphenyl)-λ4-tellanyl)methyl)-5,6-dihydrothiazolo[2,3-c][1,2,4]triazol-1-ium chlorides and annulation of the thiazoline cycle. The introduction of aryl and heteryl substituents of different nature does not affect the regioselectivity of the heteroannulation process.

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Aryltellurochlorination of 5-Aryl(heteryl)substituted N-Allyl-1,2,4-Triazole-3-Thione Derivatives

Onisko

2023

Ukr. Chem. Journ.

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Synthesis, Crystal Structure, Spectral Characterization and Antifungal Activity of Novel Phenolic Acid Triazole Derivatives

Xiao,

Song,

Xiong

et al. 2023

Molecules

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At present, phenolic acid derivatives and triazole derivatives have a good antifungal effect, which has attracted widespread attention. A series of novel phenolic acid triazole derivatives were synthesized, and their structures were characterized by IR, MS, NMR, and X-ray crystal diffraction. Compound methyl 4-(2-bromoethoxy)benzoate, methyl 4-(2-(1H-1,2,4-triazol-1-yl) ethoxy)benzoate, 4-(2-(1H-1,2,4-triazol-1-yl)ethoxy)benzoic acid and 4-(2-(1H-1,2,4-triazol-1-yl) ethoxy)-3-methoxybenzoic acid crystallize in the monoclinic system with space group P21/n, the monoclinic system with space group P21, the monoclinic system with space group P21 and the orthorhombic system with space group Pca21, respectively. At a concentration of 100 μg/mL and 200 μg/mL, the antifungal activity against seven plant pathogen fungi was determined. Compound methyl 4-(2-bromoethoxy)benzoate has the best inhibitory effect on Rhizoctonia solani AG1, and the inhibitory rate reached 88.6% at 200 μg/mL. The inhibitory rates of compound methyl 4-(2-(1H-1,2,4-triazol-1-yl) ethoxy)benzoate against Fusarium moniliforme and Sphaeropsis sapinea at a concentration of 200 μg/mL were 76.1% and 75.4%, respectively, which were better than that of carbendazim.

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Synthesis and Antimicrobial Activity of Functional Derivatives of thiazolo[ 2,3-c][1,2,4]triazoles

Cited by 2 publications

References 34 publications

Aryltellurochlorination of 5-Aryl(heteryl)substituted N-Allyl-1,2,4-Triazole-3-Thione Derivatives

Aryltellurochlorination of 5-Aryl(heteryl)substituted N-Allyl-1,2,4-Triazole-3-Thione Derivatives

Synthesis, Crystal Structure, Spectral Characterization and Antifungal Activity of Novel Phenolic Acid Triazole Derivatives

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