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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Hauptverfasser:	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
Sprache:	English
Veröffentlicht:	2023
Schlagworte:	5-amino-3-cyanomethyl-1H-pyrazole-4-carbonitrile Pyrazolo[1,5-a][1,3,5]triazines Mannich reaction Growth-promoting effect Antidote activity
Online Zugang:	https://dspace.ncfu.ru/handle/20.500.12258/25522
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id	ir-20.500.12258-25522
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spelling	ir-20.500.12258-255222023-09-20T13:41:06Z 7-(2-Aryl-1-cyanovinyl)-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles: Synthesis and Biological Activity Dotsenko, V. V. Доценко, В. В. Strelkov, V. D. Стрелков, В. Д. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В. 5-amino-3-cyanomethyl-1H-pyrazole-4-carbonitrile Pyrazolo[1,5-a][1,3,5]triazines Mannich reaction Growth-promoting effect Antidote 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 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. 2023-09-20T13:40:26Z 2023-09-20T13:40:26Z 2023 Статья 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 http://hdl.handle.net/20.500.12258/25522 en Russian Journal of General Chemistry application/pdf application/pdf
institution	СКФУ
collection	Репозиторий
language	English
topic	5-amino-3-cyanomethyl-1H-pyrazole-4-carbonitrile Pyrazolo[1,5-a][1,3,5]triazines Mannich reaction Growth-promoting effect Antidote activity
spellingShingle	5-amino-3-cyanomethyl-1H-pyrazole-4-carbonitrile Pyrazolo[1,5-a][1,3,5]triazines Mannich reaction Growth-promoting effect Antidote activity Dotsenko, V. V. Доценко, В. В. Strelkov, V. D. Стрелков, В. Д. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В. 7-(2-Aryl-1-cyanovinyl)-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles: Synthesis and Biological Activity
description	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.
format	Статья
author	Dotsenko, V. V. Доценко, В. В. Strelkov, V. D. Стрелков, В. Д. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В.
author_facet	Dotsenko, V. V. Доценко, В. В. Strelkov, V. D. Стрелков, В. Д. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В.
author_sort	Dotsenko, V. V.
title	7-(2-Aryl-1-cyanovinyl)-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles: Synthesis and Biological Activity
title_short	7-(2-Aryl-1-cyanovinyl)-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles: Synthesis and Biological Activity
title_full	7-(2-Aryl-1-cyanovinyl)-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles: Synthesis and Biological Activity
title_fullStr	7-(2-Aryl-1-cyanovinyl)-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles: Synthesis and Biological Activity
title_full_unstemmed	7-(2-Aryl-1-cyanovinyl)-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles: Synthesis and Biological Activity
title_sort	7-(2-aryl-1-cyanovinyl)-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles: synthesis and biological activity
publishDate	2023
url	https://dspace.ncfu.ru/handle/20.500.12258/25522
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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

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