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Title: 7-(2-Aryl-1-cyanovinyl)-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles: Synthesis and Biological Activity
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.
Keywords: 5-amino-3-cyanomethyl-1H-pyrazole-4-carbonitrile;Pyrazolo[1,5-a][1,3,5]triazines;Mannich reaction;Growth-promoting effect;Antidote activity
Issue Date: 2023
Citation: Stepanova, S.F., Semenova, A.M., Dotsenko, V.V., Strelkov, V.D., Temerdashev, A.Z., Gasyuk, O.A., Volchenko, N.N., Aksenov, N.A., Aksenova, I.V. 7-(2-Aryl-1-cyanovinyl)-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles: Synthesis and Biological Activity // Russian Journal of General Chemistry. - 2023. - 93 (6), pp. 1360-1373. - DOI: 10.1134/S1070363223060063
Series/Report no.: Russian Journal of General Chemistry
Abstract: 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.
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