Synthesis and cytotoxicity of oxindoles dispiro derivatives with thiohydantoin and adamantane fragments
Dmitriy A Skvortsov
1, 2
,
Dmitry Skvortsov
1, 2
,
Marina A Kalinina
3
,
Viktor A. Tafeenko
1
,
Kin Keung Lee
4
,
Gennady M Butov
4
,
Gennady M. Butov
4
,
Nikolai V. Zyk
1
,
Alexander G. Majouga
1, 5, 6
,
Elena K Beloglazkina
1
,
5
Тип публикации: Journal Article
Дата публикации: 2020-02-12
scimago Q4
wos Q3
БС3
SJR: 0.264
CiteScore: 2.6
Impact factor: 1.6
ISSN: 10426507, 15635325, 10267719
Organic Chemistry
Biochemistry
Inorganic Chemistry
Краткое описание
Abstract An effective and highly regio- and diastereoselective one-pot synthesis of two types of dispiro heterocyclic systems (2-thioxodispiro[imidazolidine-4,3′-pyrrolidine-2′,3″-indoline]-2″,5-diones and 2-thioxodispiro[imidazolidine-4,3′-pyrrolidine-4′,3″-indoline]-2″,5-diones) comprising pyrrolidinyl-oxindole, thiohydantoin and adamantane moieties has been developed based on a 1,3-dipolar cycloaddition of azomethine ylides, generated from isatin and sarcosine or formaldehyde and sarcosine, to adamantane-containing electron-deficient alkenes. Several molecules have demonstrated a considerable cytotoxicity against A549, HEK293T, MCF7 and VA13 cancer cell lines. The possible mechanism of anticancer activity of the synthesized compounds based on literature data may be the inhibition of p53/MDM2 interaction; however, we did not observe significant p53 activation using a reporter construction in A549 cell line in the relevant concentration range. Graphical Abstract
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Kukushkin M. E. et al. Synthesis and cytotoxicity of oxindoles dispiro derivatives with thiohydantoin and adamantane fragments // Phosphorus, Sulfur and Silicon and the Related Elements. 2020. Vol. 195. No. 7. pp. 544-555.
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Kukushkin M. E., Skvortsov D. A., Skvortsov D., Kalinina M. A., Tafeenko V. A., Burmistrov V. V., Lee K. K., Butov G. M., Butov G. M., Zyk N. V., Majouga A. G., Beloglazkina E. K., Beloglazkina E. K. Synthesis and cytotoxicity of oxindoles dispiro derivatives with thiohydantoin and adamantane fragments // Phosphorus, Sulfur and Silicon and the Related Elements. 2020. Vol. 195. No. 7. pp. 544-555.
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TY - JOUR
DO - 10.1080/10426507.2020.1723590
UR - https://www.tandfonline.com/doi/full/10.1080/10426507.2020.1723590
TI - Synthesis and cytotoxicity of oxindoles dispiro derivatives with thiohydantoin and adamantane fragments
T2 - Phosphorus, Sulfur and Silicon and the Related Elements
AU - Kukushkin, Maxim E.
AU - Skvortsov, Dmitriy A
AU - Skvortsov, Dmitry
AU - Kalinina, Marina A
AU - Tafeenko, Viktor A.
AU - Burmistrov, Vladimir V
AU - Lee, Kin Keung
AU - Butov, Gennady M
AU - Butov, Gennady M.
AU - Zyk, Nikolai V.
AU - Majouga, Alexander G.
AU - Beloglazkina, Elena K
AU - Beloglazkina, Elena K.
PY - 2020
DA - 2020/02/12
PB - Taylor & Francis
SP - 544-555
IS - 7
VL - 195
SN - 1042-6507
SN - 1563-5325
SN - 1026-7719
ER -
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@article{2020_Kukushkin,
author = {Maxim E. Kukushkin and Dmitriy A Skvortsov and Dmitry Skvortsov and Marina A Kalinina and Viktor A. Tafeenko and Vladimir V Burmistrov and Kin Keung Lee and Gennady M Butov and Gennady M. Butov and Nikolai V. Zyk and Alexander G. Majouga and Elena K Beloglazkina and Elena K. Beloglazkina},
title = {Synthesis and cytotoxicity of oxindoles dispiro derivatives with thiohydantoin and adamantane fragments},
journal = {Phosphorus, Sulfur and Silicon and the Related Elements},
year = {2020},
volume = {195},
publisher = {Taylor & Francis},
month = {feb},
url = {https://www.tandfonline.com/doi/full/10.1080/10426507.2020.1723590},
number = {7},
pages = {544--555},
doi = {10.1080/10426507.2020.1723590}
}
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MLA
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Kukushkin, Maxim E., et al. “Synthesis and cytotoxicity of oxindoles dispiro derivatives with thiohydantoin and adamantane fragments.” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 195, no. 7, Feb. 2020, pp. 544-555. https://www.tandfonline.com/doi/full/10.1080/10426507.2020.1723590.