Phosphorus, Sulfur and Silicon and the Related Elements, volume 195, issue 7, pages 544-555

Synthesis and cytotoxicity of oxindoles dispiro derivatives with thiohydantoin and adamantane fragments

Kukushkin Maxim E. 1
Skvortsov Dmitry 1, 2
Skvortsov Dmitriy A 1, 2
Kalinina Marina A 3
Tafeenko Viktor A. 1
Burmistrov Vladimir V 4
Butov Gennady M 4
Butov Gennady M. 4
Zyk Nikolai V. 1
Majouga Alexander G. 1, 5, 6
Beloglazkina Elena K 1
Publication typeJournal Article
Publication date2020-02-12
Quartile SCImago
Q4
Quartile WOS
Q4
Impact factor1.3
ISSN10426507, 15635325
Organic Chemistry
Biochemistry
Inorganic Chemistry
Abstract
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.
GOST all authors (up to 50) Copy
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.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1080/10426507.2020.1723590
UR - https://doi.org/10.1080%2F10426507.2020.1723590
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 - Kalinina, Marina A
AU - Tafeenko, Viktor A.
AU - Burmistrov, Vladimir V
AU - Butov, Gennady M
AU - Zyk, Nikolai V.
AU - Majouga, Alexander G.
AU - Beloglazkina, Elena K
AU - Skvortsov, Dmitry
AU - Lee, Kin Keung
AU - Butov, Gennady M.
AU - Beloglazkina, Elena K.
PY - 2020
DA - 2020/02/12 00:00:00
PB - Taylor & Francis
SP - 544-555
IS - 7
VL - 195
SN - 1042-6507
SN - 1563-5325
ER -
BibTex |
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BibTex Copy
@article{2020_Kukushkin,
author = {Maxim E. Kukushkin and Dmitriy A Skvortsov and Marina A Kalinina and Viktor A. Tafeenko and Vladimir V Burmistrov and Gennady M Butov and Nikolai V. Zyk and Alexander G. Majouga and Elena K Beloglazkina and Dmitry Skvortsov and Kin Keung Lee and Gennady M. Butov 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://doi.org/10.1080%2F10426507.2020.1723590},
number = {7},
pages = {544--555},
doi = {10.1080/10426507.2020.1723590}
}
MLA
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MLA Copy
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://doi.org/10.1080%2F10426507.2020.1723590.
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