Home / Publications / Synthesis and cytotoxic activity of novel 4-amino-5-cyano-2-sulfonylpyrimidines

Synthesis and cytotoxic activity of novel 4-amino-5-cyano-2-sulfonylpyrimidines

Dmitry Aleksandrovich Khochenkov 1, 2
Dmitry Aleksandrovich Khochenkov
Yulia A Khochenkova 2
Yulia A Khochenkova
Yulia S Machkova 2
Yulia S Machkova
Rovshan E Gasanov 1
Rovshan E Gasanov
Eugenia V Stepanova 2
Eugenia V Stepanova
Alexander Siyasatovich Bunev 1
Alexander Siyasatovich Bunev
Published 2020-08-31
CommunicationVolume 30, Issue 5, 604-606
3
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Khochenkov D. A. et al. Synthesis and cytotoxic activity of novel 4-amino-5-cyano-2-sulfonylpyrimidines // Mendeleev Communications. 2020. Vol. 30. No. 5. pp. 604-606.
GOST all authors (up to 50) Copy
Khochenkov D. A., Khochenkova Y. A., Machkova Y. S., Gasanov R. E., Stepanova E. V., Bunev A. S. Synthesis and cytotoxic activity of novel 4-amino-5-cyano-2-sulfonylpyrimidines // Mendeleev Communications. 2020. Vol. 30. No. 5. pp. 604-606.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2020.09.017
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.017
TI - Synthesis and cytotoxic activity of novel 4-amino-5-cyano-2-sulfonylpyrimidines
T2 - Mendeleev Communications
AU - Khochenkov, Dmitry Aleksandrovich
AU - Khochenkova, Yulia A
AU - Machkova, Yulia S
AU - Gasanov, Rovshan E
AU - Stepanova, Eugenia V
AU - Bunev, Alexander Siyasatovich
PY - 2020
DA - 2020/08/31
PB - Mendeleev Communications
SP - 604-606
IS - 5
VL - 30
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2020_Khochenkov,
author = {Dmitry Aleksandrovich Khochenkov and Yulia A Khochenkova and Yulia S Machkova and Rovshan E Gasanov and Eugenia V Stepanova and Alexander Siyasatovich Bunev},
title = {Synthesis and cytotoxic activity of novel 4-amino-5-cyano-2-sulfonylpyrimidines},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Aug},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.017},
number = {5},
pages = {604--606},
doi = {10.1016/j.mencom.2020.09.017}
}
MLA
Cite this
MLA Copy
Khochenkov, Dmitry Aleksandrovich, et al. “Synthesis and cytotoxic activity of novel 4-amino-5-cyano-2-sulfonylpyrimidines.” Mendeleev Communications, vol. 30, no. 5, Aug. 2020, pp. 604-606. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.017.

Keywords

cancer cell lines
cytotoxic activity
heterocyclization
isothiouronic salts
nitriles
pyrimidines
sulfones

Abstract

Novel 4-amino-5-cyano-2-sulfonylpyrimidines were prepared based on three-component cyclization between isothiouronium salts, benzaldehydes and malononitrile, followed by oxidation of the sulfide moiety with Oxone. The cytotoxic activity of the synthesized compounds, as well as the induction of apoptosis, inhibition of the cell cycle and proliferation tests were performed on selected cancer cell lines A431, A549, A375, HCT 116, MCF7, LNCap and SH-SY5Y.

References

2.
Advances in studies of tyrosine kinase inhibitors and their acquired resistance
Jiao Q., Bi L., Ren Y., Song S., Wang Q., Wang Y.
Molecular Cancer, 2018
3.
Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives.
Ma D., Wang L., Lai Q., Peng K., Li X., Li Z., Liu L., Luo Z., Liu S.
Bioorganic and Medicinal Chemistry Letters, 2018
4.
Egorov V.A., Gimalova F.A., Zileeva Z.R., Zainullina L.F., Vakhitova Y.V., Miftakhov M.S.
Mendeleev Communications, 2019
5.
Oxidative nucleophilic substitution selectively produces cambinol derivatives with antiproliferative activity on bladder cancer cell lines.
Botta L., Filippi S., Bizzarri B.M., Meschini R., Caputo M., Proietti-De-Santis L., Iside C., Nebbioso A., Gualandi G., Saladino R.
Bioorganic and Medicinal Chemistry Letters, 2019
6.
Bagautdinova R.K., Vagapova L.I., Smolobochkin A.V., Gazizov A.S., Burilov A.R., Pudovik M.A., Voloshina A.D.
Mendeleev Communications, 2019
7.
Vostrikov N.S., Spirikhin L.V., Lobov A.N., Gimazetdinov A.M., Zileeva Z.R., Vakhitova Y.V., Macaev Z.R., Pivnitsky K.K., Miftakhov M.S.
Mendeleev Communications, 2019
8.
Chimeric tyrosine kinase-HDAC inhibitors as antiproliferative agents
Uecker A., Sicker M., Beckers T., Mahboobi S., Hägerstrand D., Östman A., Böhmer F.
Anti-Cancer Drugs, 2010
9.
Zorina A.D., Nikiforova N.S., Zarubaev V.V., Marchenko S.A., Selivanov S.I., Starova G.L., Mehtiev A.R., Rodionov E.I., Rodionova A.A., Trifonov R.E.
Mendeleev Communications, 2019
10.
Biologically active azolo-1,2,4-triazines and azolopyrimidines
Rusinov V.L., Charushin V.N., Chupakhin O.N.
Russian Chemical Bulletin, 2018
11.
ZD1839 (IRESSA™): a selective EGFR-TK inhibitor
Ranson M., Mansoor W., Jayson G.
Expert Review of Anticancer Therapy, 2002
12.
AZD9291, an irreversible EGFR TKI, overcomes T790M-mediated resistance to EGFR inhibitors in lung cancer.
Cross D.A., Ashton S.E., Ghiorghiu S., Eberlein C., Nebhan C.A., Spitzler P.J., Orme J.P., Finlay M.R., Ward R.A., Mellor M.J., Hughes G., Rahi A., Jacobs V.N., Brewer M.R., Ichihara E., et. al.
Cancer Discovery, 2014
13.
Specific Targeted Therapy of Chronic Myelogenous Leukemia with Imatinib
Deininger M.W., Druker B.J.
Pharmacological Reviews, 2003
14.
Synthesis and antimicrobial evaluation of novel substituted pyrimidine scaffold
Ghodasara H.B., Trivedi A.R., Kataria V.B., Patel B.G., Shah V.H.
Medicinal Chemistry Research, 2013
15.
Synthesis of a 2,4,6-trisubstituted 5-cyano-pyrimidine library and evaluation of its immunosuppressive activity in a Mixed Lymphocyte Reaction assay
Stella A., Van Belle K., De Jonghe S., Louat T., Herman J., Rozenski J., Waer M., Herdewijn P.
Bioorganic and Medicinal Chemistry, 2013
16.
2,4,6-Triaminopyrimidine as a Novel Hinge Binder in a Series of PI3Kδ Selective Inhibitors.
Patel L., Chandrasekhar J., Evarts J., Haran A.C., Ip C., Kaplan J.A., Kim M., Koditek D., Lad L., Lepist E., McGrath M.E., Novikov N., Perreault S., Puri K.D., Somoza J.R., et. al.
Journal of Medicinal Chemistry, 2016
17.
5-Cyanopyrimidine derivatives as a novel class of potent, selective, and orally active inhibitors of p38alpha MAP kinase.
Liu C., Wrobleski S.T., Lin J., Ahmed G., Metzger A., Wityak J., Gillooly K.M., Shuster D.J., McIntyre K.W., Pitt S., Shen D.R., Zhang R.F., Zhang H., Doweyko A.M., Diller D., et. al.
Journal of Medicinal Chemistry, 2005
18.
High-Throughput Screening and Hit Validation of Extracellular-Related Kinase 5 (ERK5) Inhibitors.
Myers S.M., Bawn R.H., Bisset L.C., Blackburn T.J., Cottyn B., Molyneux L., Wong A., Cano C., Clegg W., Harrington R.W., Leung H., Rigoreau L., Vidot S., Golding B.T., Griffin R.J., et. al.
ACS Combinatorial Science, 2016
19.
Facile iterative synthesis of 2,5-terpyrimidinylenes as nonpeptidic alpha-helical mimics.
Anderson L., Zhou M., Sharma V., McLaughlin J.M., Santiago D.N., Fronczek F.R., Guida W.C., McLaughlin M.L.
Journal of Organic Chemistry, 2010