6-(Tetrazol-5-yl)-7-aminoazolo[1,5-a]pyrimidines as Novel Potent CK2 Inhibitors
Электронный научный архив УРФУ
Информация об архиве | Просмотр оригинала| Поле | Значение | |
| Заглавие |
6-(Tetrazol-5-yl)-7-aminoazolo[1,5-a]pyrimidines as Novel Potent CK2 Inhibitors
|
|
| Автор |
Urakov, G. V.
Savateev, K. V. Kotovskaya, S. K. Rusinov, V. L. Spasov, A. A. Babkov, D. A. Sokolova, E. V. |
|
| Тематика |
AZOLO[1,5-A]PYRIMIDINES
CASEIN KINASE 2 INHIBITORS REGIOSELECTIVITY STRUCTURE-ACTIVITY RELATIONSHIP TETRAZOLES CASEIN KINASE II DRUG DESIGN MOLECULAR STRUCTURE NITRILES PYRIMIDINES SALTS SODIUM STRUCTURE-ACTIVITY RELATIONSHIP TETRAZOLES CASEIN KINASE II INORGANIC SALT NITRILE PYRIMIDINE DERIVATIVE SODIUM TETRAZOLE DERIVATIVE CHEMICAL STRUCTURE DRUG DESIGN STRUCTURE ACTIVITY RELATION |
|
| Описание |
In this work, we describe the design, synthesis, and structure-activity relationship of 6-(tetrazol-5-yl)-7-aminoazolo[1,5-a]pyrimidines as inhibitors of Casein kinase 2 (CK2). At first, we optimized the reaction conditions for the azide-nitrile cycloaddition in the series of 6-cyano-7-aminoazolopyridimines and sodium azide. The regioselectivity of this process has been shown, as the cyano group of the pyrimidine cycle was converted to tetrazole while the nitrile of the azole fragment did not react. The desired tetrazolyl-azolopyrimidines were obtained in a moderate to excellent yields (42–95%) and converted further to water soluble sodium salts by the action of sodium bicarbonate. The obtained 6-(tetrazol-5-yl)-7-aminopyrazolo[1,5-a]pyrimidines 2a–k and their sodium salts 3a–c, 3g–k showed nano to low micromolar range of CK2 inhibition while corresponding [1,2,4]triazolopyrimidines 10a–k were less active (IC50 > 10 µM). The leader compound 3-phenyl-6-(tetrazol-5-yl)-7-aminopyrazolo[1,5-a]pyrimidine 2i as CK2 inhibitor showed IC50 45 nM. © 2022 by the authors.
Ministry of Education and Science of the Russian Federation, Minobrnauka, (FEUZ-2020–0058, H687.42B.223/20) This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation, State Contract № FEUZ-2020–0058 (H687.42B.223/20). |
|
| Дата |
2024-04-08T11:06:42Z
2024-04-08T11:06:42Z 2022 |
|
| Тип |
Article
Journal article (info:eu-repo/semantics/article) Published version (info:eu-repo/semantics/publishedVersion) |
|
| Идентификатор |
Urakov, GV, Savateev, KV, Kotovskaya, SK, Rusinov, VL, Spasov, AA, Babkov, DA & Sokolova, EV 2022, '6-(Tetrazol-5-yl)-7-aminoazolo[1,5-a]pyrimidines as Novel Potent CK2 Inhibitors', Molecules, Том. 27, № 24, 8697. https://doi.org/10.3390/molecules27248697
Urakov, G. V., Savateev, K. V., Kotovskaya, S. K., Rusinov, V. L., Spasov, A. A., Babkov, D. A., & Sokolova, E. V. (2022). 6-(Tetrazol-5-yl)-7-aminoazolo[1,5-a]pyrimidines as Novel Potent CK2 Inhibitors. Molecules, 27(24), [8697]. https://doi.org/10.3390/molecules27248697 1420-3049 Final All Open Access; Gold Open Access; Green Open Access https://www.mdpi.com/1420-3049/27/24/8697/pdf?version=1670504257 https://www.mdpi.com/1420-3049/27/24/8697/pdf?version=1670504257 http://elar.urfu.ru/handle/10995/131338 10.3390/molecules27248697 85144578785 |
|
| Язык |
en
|
|
| Права |
Open access (info:eu-repo/semantics/openAccess)
cc-by https://creativecommons.org/licenses/by/4.0/ |
|
| Формат |
application/pdf
|
|
| Издатель |
MDPI
|
|
| Источник |
Molecules
Molecules |
|