Standard

6-(Tetrazol-5-yl)-7-aminoazolo[1,5-a]pyrimidines as Novel Potent CK2 Inhibitors. / Urakov, Grigoriy V.; Savateev, Konstantin V.; Kotovskaya, Svetlana K. et al.
In: Molecules, Vol. 27, No. 24, 8697, 07.12.2022.

Research output: Contribution to journal › Article › peer-review

Harvard

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, vol. 27, no. 24, 8697. https://doi.org/10.3390/molecules27248697

APA

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

Vancouver

Urakov GV, Savateev KV, Kotovskaya SK, Rusinov VL, Spasov AA, Babkov DA et al. 6-(Tetrazol-5-yl)-7-aminoazolo[1,5-a]pyrimidines as Novel Potent CK2 Inhibitors. Molecules. 2022 Dec 7;27(24):8697. doi: 10.3390/molecules27248697

Author

Urakov, Grigoriy V. ; Savateev, Konstantin V. ; Kotovskaya, Svetlana K. et al. / 6-(Tetrazol-5-yl)-7-aminoazolo[1,5-a]pyrimidines as Novel Potent CK2 Inhibitors. In: Molecules. 2022 ; Vol. 27, No. 24.

BibTeX

@article{35e9f1b95a2041b98ee7989d158d22b7,
title = "6-(Tetrazol-5-yl)-7-aminoazolo[1,5-a]pyrimidines as Novel Potent CK2 Inhibitors",
abstract = "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.",
author = "Urakov, {Grigoriy V.} and Savateev, {Konstantin V.} and Kotovskaya, {Svetlana K.} and Rusinov, {Vladimir L.} and Spasov, {Alexandr A.} and Babkov, {Denis A.} and Sokolova, {Elena V.}",
note = "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).",
year = "2022",
month = dec,
day = "7",
doi = "10.3390/molecules27248697",
language = "English",
volume = "27",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "24",

}

RIS

TY - JOUR

T1 - 6-(Tetrazol-5-yl)-7-aminoazolo[1,5-a]pyrimidines as Novel Potent CK2 Inhibitors

AU - Urakov, Grigoriy V.

AU - Savateev, Konstantin V.

AU - Kotovskaya, Svetlana K.

AU - Rusinov, Vladimir L.

AU - Spasov, Alexandr A.

AU - Babkov, Denis A.

AU - Sokolova, Elena V.

N1 - 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).

PY - 2022/12/7

Y1 - 2022/12/7

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85144578785

U2 - 10.3390/molecules27248697

DO - 10.3390/molecules27248697

M3 - Article

VL - 27

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 24

M1 - 8697

ER -

ID: 33229429