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7-(2-Aryl-1-cyanovinyl)-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles: Synthesis and Biological Activity

A new method was proposed for the preparation of 5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile by reaction of the potassium salt of malononitrile dimer with hydrazinium sulfate. The reaction of 5-amino-3(cyanomethyl)-1H-pyrazole-4-carbonitrile with aromatic aldehydes in the presence of catalyti...

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Bibliographic Details
Main Authors: Dotsenko, V. V., Доценко, В. В., Strelkov, V. D., Стрелков, В. Д., Aksenov, N. A., Аксенов, Н. А., Aksenova, I. V., Аксенова, И. В.
Format: Статья
Language:English
Published: 2023
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Online Access:https://dspace.ncfu.ru/handle/20.500.12258/25522
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Summary:A new method was proposed for the preparation of 5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile by reaction of the potassium salt of malononitrile dimer with hydrazinium sulfate. The reaction of 5-amino-3(cyanomethyl)-1H-pyrazole-4-carbonitrile with aromatic aldehydes in the presence of catalytic amounts of morpholine leads to the formation of Knoevenagel condensation products. Aminomethylation of the resulting (Z)-5-amino-3-(2-aryl-1-cyanovinyl)-1H-pyrazole-4-carbonitriles with primary aromatic amines and excess aqueous HCHO in refluxing DMF leads to the formation of 7-(2-aryl-1-cyanovinyl)-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. Bioavailability parameters were studied in silico, and possible protein targets were predicted by protein-ligand docking. In an in vitro experiment on cultures of E. coli, S. aureus and B. pumilis, 5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile does not show any noticeable antibacterial effect. At the same time, three compounds of the pyrazolo[1,5-a][1,3,5]triazine series showed a pronounced antidote effect against the herbicide 2,4-D on sunflower seedlings in a laboratory experiment, for one compound a noticeable growth-stimulating effect was noted.