Reactivity of 3-substituted pyrazole-5-diazonium salts towards 3-azolyl enamines. Synthesis of novel 3-azolylpyrazolo[5,1-c][1,2,4]triazines

Alexeeva, Daria L.; Садчикова, Е. В.; Волкова, Н. Н.; Efimov, Ilya; Jacobs, Jeroen; Meervelt, Luc Van; Dehaen, Wim; Бакулев, В. А.

doi:10.3998/ark.5550190.p009.571

Cited by 7 publications

(5 citation statements)

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“…The attempts to aromatize DATs–NMe 2 10 , 11a to azolo[5,1- c ][ 1 , 2 , 4 ]triazines, as occurred in the reaction of azole diazonium salts with the enamines [ 25 ], by the addition of glacial AcOH, as well as catalytic amounts of H 2 SO 4 or equimolar amounts of HBF 4 , failed. As a result, hydrolysis to the corresponding non-aromatic of DAT–OH 12 , 13a proceeded ( Scheme 6 ).…”

Section: Resultsmentioning

confidence: 99%

“…The reaction of azole diazonium salts 1 [ 24 ] with heterocyclic enamines 2 and 3 leads to azolo[5,1- c ][1,2,4]triazines 4 and 5 [ 25 ] ( Scheme 1 ). Analogous azolotriazines were synthesized previously by using enamines, obtained from various secondary linear N , N -dialkylamines, and cyclic amines—pyrrolidine, piperidine, morpholine [ 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 ].…”

Section: Introductionmentioning

confidence: 99%

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Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties

et al. 2023

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New fluorescent dyes containing an assembled 1,4-dihydroazolo[5,1-c][1,2,4]triazine (DAT) core and an isoxazole ring were synthesized through a reaction between diazopyrazole or diazoimidazoles and isoxazolyl-derived enamines in mild conditions. The photophysical characteristics (maxima absorption and emission, Stokes shifts, fluorescent quantum yields, and fluorescence lifetimes) of the new fluorophores were obtained. The prepared DATs demonstrated emission maxima ranging within 433–487 nm, quantum yields within 6.1–33.3%, and a large Stokes shift. The photophysical characteristics of representative DAT examples were studied in ten different solvents. Specific (hydrogen bonds) and non-specific (dipole–dipole) intermolecular and intramolecular interactions were analyzed using XRD data and spectral experiments. Solvatochromism was analyzed using Lippert–Mataga and Dimroth–Reichardt plots, revealing the relationship between the DAT structure and the nature of solute–solvent interactions. The significant advantages of DATs are the fluorescence of their powders (QY up to 98.7%). DAT-NMe2 10 expressed bright aggregation-induced emission (AIE) behavior in DMSO and THF as the water content increased. The numerous possible variations of the structures of the heterocycles included in the DATs, as well as substituents, create excellent prospects for adjusting their photophysical and physicochemical properties.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties

et al. 2023

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“…Three new azoloazine derivatives tested in this work were synthesized at the Yeltsin Ural Federal University [13]. Figure 1 demonstrates that substance 1 is a tetrazine derivative, and substances 2 and 3 are triazine derivatives.…”

Section: Methodsmentioning

confidence: 99%

“…The Siberian Journal of Clinical and Experimental Medicine сии Б.Н. Ельцина [13]. Рисунок 1 демонстрирует, что вещество 1 является производным тетразина, а вещества 2 и 3 -производными триазина.…”

Section: сибирский журнал клинической и экспериментальной медициныunclassified

Effect of new azoloazine derivatives with potential antitumor activity on energy metabolism in MCF-7 and Vero cell cultures

Al-Humairi

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et al. 2023

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Introduction. The work presents the results of studying the effects of three new azoloazine derivatives on oxidative glucose metabolism in order to select substances with the most acceptable characteristics for further preclinical study as potential antitumor agents, including for breast cancer chemotherapy.Aim. The aim of the work is to identify the metabolic properties of new azoloazine derivatives in terms of their effect on glucose metabolism using a culture of MCF-7 tumor cells and Vero non-tumor cells.Material and Methods. The testing on cell cultures was the main method used in the work, and all tested compounds were applied in final concentrations from 2.5 μmol/L. The comparison drug was epirubicin in the same concentration. The biochemical techniques included the determination of lactate production using commercial Olvex Diagnosticum kits and the determination of oxygen consumption by cells using the Seahorse XFe24 Analyzer for cellular metabolism. The results were processed statistically.Results. Lactate production in MCF-7 and Vero cell cultures decreased by more than half in the presence of 3-Cyclohexyl4-oxoimidazo[5,1-d]-[1,2,3,5]tetrazine-8-N-piperidinyl-carboxamide, and oxygen consumption decreased by 19-40%, which was the maximum effect among the studied azoloazine derivatives. Diethyl ether of 4-aminoimidazo[5,1-c][1,2,4]triazine-3,8dicarboxylic acid and 4-Amino-8-ethoxycarbonyl-imidazo[5,1-c][1,2,4]triazine-3-N-(p-toluyl)carboxamide were similar in their metabolic effects to the comparison drug epirubicin. They reduced lactate production in MCF-7 and Vero cell culture by a third and by 21–22%, respectively. Oxygen consumption in MCF-7 cell culture decreased by 14–17%, in Vero cell culture it decreased by 18–24%.Conclusion. The data obtained allow us to consider the (3-Cyclohexyl-4-oxoimidazo[5,1-d]-[1,2,3,5]tetrazine-8-N-piperidinylcarboxamide as the leader among new azoloazine derivatives and recommend it for further preclinical study as a potential antitumor agent.

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“…In a preliminary report, 20 we described the synthesis of novel 3-thiadiazolyl-pyrazolo[5,1- c ][1,2,4]triazines 4a–e in a reaction between 3-substituted pyrazole-5-diazonium salts 1a–e ( ν N2 = 2270–2280 cm −1 ) and thiadiazolyl enamines 3a , b (Scheme 1). On the other hand, 3-aryl- or 3-methyl substituted 5-diazopyrazoles 2a–e ( ν N2 = 2130–2150 cm −1 ) failed to produce the target products under similar conditions.…”

Section: Introductionmentioning

confidence: 99%

Non-aromatic azolo[5,1-c][1,2,4]triazines: a pot, atom and step economic (PASE) synthesis, mechanistic insight and fluorescence properties

et al. 2022

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Reactivity of 3-substituted pyrazole-5-diazonium salts towards 3-azolyl enamines. Synthesis of novel 3-azolylpyrazolo[5,1-c][1,2,4]triazines

Cited by 7 publications

References 31 publications

Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties

Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties

Effect of new azoloazine derivatives with potential antitumor activity on energy metabolism in MCF-7 and Vero cell cultures

Non-aromatic azolo[5,1-c][1,2,4]triazines: a pot, atom and step economic (PASE) synthesis, mechanistic insight and fluorescence properties

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