Halo-heterocyclization of butenyl(prenyl)thioethers of 4,5-diphenyl-1,2,4-triazol-3-thiole into triazolo[5,1-b] [1,3]thiazinium systems: experimental and theoretical evolution

Korol, Nataliya; Slivka, Mikhailo; Fizer, Maksym; Baumer, V. N.; Lendel, V. G.

doi:10.1007/s00706-019-02545-w

Cited by 15 publications

(2 citation statements)

References 54 publications

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“…[88] Electrophilic heterocyclization of 4,5-disubstituted thioethers of 1,2,4-triazole leads to the formation of the target thiazinotriazolium salts 37. [55,89] The action of selenium and tellurium tetrahalides on cinnamyl thioethers does not lead to annulation of the additional cycle, instead molecular complexes 38 were formed (Scheme 27). [55] In the 13C NMR spectra of system 37, the signal of C-5 atom is at 40 to 42 ppm.…”

Section: Synthesis Of Thiazolo [32-b][124]triazole Derivativesmentioning

confidence: 99%

Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

Slivka

Korol

Fizer

2020

Journal of Heterocyclic Chem

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Fused heterocyclic systems with 1,2,4‐triazole scaffold arouse great interest from researchers in the branch of heterocyclic and medical chemistry because of their wide biological activities as they are considered as fungicidal, antimicrobial, analgesic, bronchodilators, antioxidant, anti‐inflammatory agents, and they are G‐quadruple stabilizers; the molecular docking data for coumarin‐containing 1,2,4‐triazoles indicate their ability to act as a urease inhibitor. Therefore, the present review aims to investigate new trends in the chemistry of heterocycles incorporating thiazolo[3,2‐b][1,2,4]triazoles, thiazolo[2,3‐c][1,2,4]triazoles, thiazino[5,1‐b][1,2,4]triazoles, thiazino[3,4‐b][1,2,4]triazoles, triazolothiazepines, and their biological characteristics. The main sections discuss: (a) the synthetic routes to the production of substituted fused heterocyclic systems, which include condensation reactions, multiple bond annulation, and the reactions of electrophilic heterocyclization. (b) Description of chemical and biological characteristics of these fused heterocycles.

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Section: Synthesis Of Thiazolo [32-b][124]triazole Derivativesmentioning

confidence: 99%

Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

Slivka

Korol

Fizer

2020

Journal of Heterocyclic Chem

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“…In our previous studies, we successfully synthesized fused 1,2,4-triazolium salts [13][14][15][16] using a low-cost, efficient, and easy workup electrophilic cyclization methodology. 17 Building upon this work, our current aim is to obtain new derivatives of 5,5'butane-bis-1,2,4-triazole, considering the potential enhancement of their biological properties due to the presence of both the butane bridge and the triazole moiety.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Evaluation and Molecular Docking Studies of Novel Series of Bis-1,2,4-Triazoles as Thymidine Phosphorylase Inhibitor

Korol,

Holovko-Kamoshenkova,

Slivka

et al. 2023

AABC

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Heterocyclic compounds have diverse biological activities and potential in drug development. This study aims to synthesize novel compounds with two 1,2,4-triazole cores and evaluate their biological properties, particularly their inhibitory activity against thymidine phosphorylase (TP), an enzyme involved in various physiological processes. Methods: The compounds were synthesized by reacting 5,5'-butane-bis-1,2,4-triazole derivatives with prenyl bromide. Characterization involved various techniques, including spectroscopy and elemental analysis. Antimicrobial potential was evaluated against bacteria and fungi, with comparative antibiotics as references. Inhibitory activity against TP was assessed, and molecular docking studies were conducted. Results: Six compounds were successfully synthesized and their structures confirmed. The synthesized triazole derivatives exhibited high biological activity, with compounds 2 and 6 showing the most promising TP inhibition. Molecular docking studies revealed interactions between compound 2 and TP, involving nine amino acids. Discussion: The synthesis of novel compounds with two 1,2,4-triazole cores contributes significantly to bis-triazole research. These compounds have potential as anti-tumor agents due to their inhibitory activity against TP, a crucial enzyme in tumor growth and metastasis. Comparative evaluation against antibiotics highlights their potency. Docking results provide insights into their interactions with TP, supporting their potential as potent TP inhibitors. Further research should focus on evaluating their efficacy in biological models, understanding their mechanisms of action, and optimizing their activities. Conclusion:The synthesized compounds with two 1,2,4-triazole cores exhibit significant biological activity, including strong TP inhibition and broad-spectrum antimicrobial effects. These findings emphasize their potential as anti-tumor agents and the need for further exploration and optimization. Future research should focus on evaluating their efficacy in biological models, understanding their mechanisms of action, and developing more potent bis-triazole derivatives for drug discovery efforts. The combined results from assays and docking studies support the therapeutic potential of these compounds as anti-tumor agents.

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New [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium cationic surfactant as a stabilizer of silver and gold nanoparticles

Fizer

Slivka

et al. 2022

Appl Nanosci

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Halo-heterocyclization of butenyl(prenyl)thioethers of 4,5-diphenyl-1,2,4-triazol-3-thiole into triazolo[5,1-b] [1,3]thiazinium systems: experimental and theoretical evolution

Cited by 15 publications

References 54 publications

Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

Synthesis, Biological Evaluation and Molecular Docking Studies of Novel Series of Bis-1,2,4-Triazoles as Thymidine Phosphorylase Inhibitor

New [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium cationic surfactant as a stabilizer of silver and gold nanoparticles

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