Standard

5-Alkylamino-7-aminoazolo[1,5-a]pyrimidine-6-carbonitriles: synthetic strategies and anticancer activity in vitro. / Urakov, G. v.; Savateev, K. v.; Melekhin, V. v. et al.
In: Russian Chemical Bulletin, Vol. 72, No. 12, 01.12.2023, p. 3022-3031.

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

Harvard

Urakov, GV, Savateev, KV, Melekhin, VV, Kotovskaya, SK & Rusinov, VL 2023, '5-Alkylamino-7-aminoazolo[1,5-a]pyrimidine-6-carbonitriles: synthetic strategies and anticancer activity in vitro', Russian Chemical Bulletin, vol. 72, no. 12, pp. 3022-3031. https://doi.org/10.1007/s11172-023-4114-5

APA

Urakov, G. V., Savateev, K. V., Melekhin, V. V., Kotovskaya, S. K., & Rusinov, V. L. (2023). 5-Alkylamino-7-aminoazolo[1,5-a]pyrimidine-6-carbonitriles: synthetic strategies and anticancer activity in vitro. Russian Chemical Bulletin, 72(12), 3022-3031. https://doi.org/10.1007/s11172-023-4114-5

Vancouver

Urakov GV, Savateev KV, Melekhin VV, Kotovskaya SK, Rusinov VL. 5-Alkylamino-7-aminoazolo[1,5-a]pyrimidine-6-carbonitriles: synthetic strategies and anticancer activity in vitro. Russian Chemical Bulletin. 2023 Dec 1;72(12):3022-3031. doi: 10.1007/s11172-023-4114-5

Author

Urakov, G. v. ; Savateev, K. v. ; Melekhin, V. v. et al. / 5-Alkylamino-7-aminoazolo[1,5-a]pyrimidine-6-carbonitriles: synthetic strategies and anticancer activity in vitro. In: Russian Chemical Bulletin. 2023 ; Vol. 72, No. 12. pp. 3022-3031.

BibTeX

@article{07f08d3bf86d464286e0434bb9a4d5d0,
title = "5-Alkylamino-7-aminoazolo[1,5-a]pyrimidine-6-carbonitriles: synthetic strategies and anticancer activity in vitro",
abstract = "The design of novel antagonists for adenosine A2a receptor (A2a AR) is a promising strategy for the development of new-generation anticancer agents. 5-Alkylamino-7-aminoazolo[1,5-a]pyrimidin-6-carbonitriles proposed in this work are close structural analogs of known nanomolar A2a AR antagonists. An efficient synthetic strategy towards the functional derivatives of the target heterocycles is cyclocondensation of aminoazoles with 2-[(alkylamino)(methylsulfanyl)methylene]malononitriles on heating in DMF in the presence of ButOK. The obtained azolopyrimidine-6-carbonitriles do not show statistically significant cytotoxic effect on human embryonic kidney cells, while 2-methyl- and 2-(furan-2-yl)azolopyrimidines inhibit the viability of lung carcinoma and hepatocellular carcinoma cells with IC50 values in the low micromolar range.",
author = "Urakov, {G. v.} and Savateev, {K. v.} and Melekhin, {V. v.} and Kotovskaya, {S. k.} and Rusinov, {V. l.}",
note = "The study was supported by the Ministry of Science and Higher Education of the Russian Federation (state contract No. FEUZ-2023-0021 (H687/42B.325/23)).",
year = "2023",
month = dec,
day = "1",
doi = "10.1007/s11172-023-4114-5",
language = "English",
volume = "72",
pages = "3022--3031",
journal = "Russian Chemical Bulletin",
issn = "1066-5285",
publisher = "Springer",
number = "12",

}

RIS

TY - JOUR

T1 - 5-Alkylamino-7-aminoazolo[1,5-a]pyrimidine-6-carbonitriles: synthetic strategies and anticancer activity in vitro

AU - Urakov, G. v.

AU - Savateev, K. v.

AU - Melekhin, V. v.

AU - Kotovskaya, S. k.

AU - Rusinov, V. l.

N1 - The study was supported by the Ministry of Science and Higher Education of the Russian Federation (state contract No. FEUZ-2023-0021 (H687/42B.325/23)).

PY - 2023/12/1

Y1 - 2023/12/1

N2 - The design of novel antagonists for adenosine A2a receptor (A2a AR) is a promising strategy for the development of new-generation anticancer agents. 5-Alkylamino-7-aminoazolo[1,5-a]pyrimidin-6-carbonitriles proposed in this work are close structural analogs of known nanomolar A2a AR antagonists. An efficient synthetic strategy towards the functional derivatives of the target heterocycles is cyclocondensation of aminoazoles with 2-[(alkylamino)(methylsulfanyl)methylene]malononitriles on heating in DMF in the presence of ButOK. The obtained azolopyrimidine-6-carbonitriles do not show statistically significant cytotoxic effect on human embryonic kidney cells, while 2-methyl- and 2-(furan-2-yl)azolopyrimidines inhibit the viability of lung carcinoma and hepatocellular carcinoma cells with IC50 values in the low micromolar range.

AB - The design of novel antagonists for adenosine A2a receptor (A2a AR) is a promising strategy for the development of new-generation anticancer agents. 5-Alkylamino-7-aminoazolo[1,5-a]pyrimidin-6-carbonitriles proposed in this work are close structural analogs of known nanomolar A2a AR antagonists. An efficient synthetic strategy towards the functional derivatives of the target heterocycles is cyclocondensation of aminoazoles with 2-[(alkylamino)(methylsulfanyl)methylene]malononitriles on heating in DMF in the presence of ButOK. The obtained azolopyrimidine-6-carbonitriles do not show statistically significant cytotoxic effect on human embryonic kidney cells, while 2-methyl- and 2-(furan-2-yl)azolopyrimidines inhibit the viability of lung carcinoma and hepatocellular carcinoma cells with IC50 values in the low micromolar range.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85183614877

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=001154671000012

U2 - 10.1007/s11172-023-4114-5

DO - 10.1007/s11172-023-4114-5

M3 - Article

VL - 72

SP - 3022

EP - 3031

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 12

ER -

ID: 52301476