Open Access
International Journal of Molecular Sciences, volume 22, issue 5, pages 1-26
Dispirooxindoles based on 2-selenoxo-imidazolidin-4-ones: Synthesis, cytotoxicity and ros generation ability
Novotortsev Vladimir K
1
,
Kukushkin Maxim E.
1, 2
,
Tafeenko Viktor A.
1
,
Timoshenko Roman V
2
,
Vasilyeva Liliya A
4
,
Tarasevich Boris N
1
,
Gorelkin Peter
2
,
Erofeev Alexander S.
1, 2
,
Majouga Alexander G.
1, 2, 5
,
Zyk Nikolai V.
1
,
2
3
Publication type: Journal Article
Publication date: 2021-03-05
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.6
ISSN: 16616596, 14220067
PubMed ID:
33807662
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Computer Science Applications
Spectroscopy
Molecular Biology
General Medicine
Abstract
A regio- and diastereoselective synthesis of two types of dispiro derivatives of 2-selenoxoimidazolidin-4-ones, differing in the position of the nitrogen atom in the central pyrrolidine ring of the spiro-fused system—namely, 2-selenoxodispiro[imidazolidine-4,3′-pyrrolidine-2′,3″-indoline]-2″,5-diones (5a-h) and 2-senenoxodispiro[imidazolidine-4,3′-pyrrolidine-4′,3″-indoline]-2″,5-diones (6a-m)—were developed based on a 1,3-dipolar cycloaddition of azomethine ylides generated from isatin and sarcosine or formaldehyde and sarcosine to 5-arylidene or 5-indolidene-2-selenoxo-tetrahydro-4H-imidazole-4-ones. Selenium-containing dispiro indolinones generally exhibit cytotoxic activity near to the activity of the corresponding oxygen and sulfur-containing derivatives. Compounds 5b, 5c, and 5e demonstrated considerable in vitro cytotoxicity in the 3-(4,5-dimethylthiazol-2-yl)2,5-diphenyl tetrazolium bromide (MTT) test (concentration of compounds that caused 50% death of cells (CC50) 7.6–8.7 μM) against the A549 cancer cell line with the VA13/A549 selectivity index 5.2–6.9; some compounds (5 and 6) increased the level of intracellular reactive oxygen species (ROS) in the experiment on A549 and PC3 cells using platinized carbon nanoelectrode. The tests for p53 activation for compounds 5 and 6 on the transcriptional reporter suggest that the investigated compounds can only have an indirect p53-dependent mechanism of action. For the compounds 5b, 6b, and 6l, the ROS generation may be one of the significant mechanisms of their cytotoxic action.
Citations by journals
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International Journal of Molecular Sciences
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International Journal of Molecular Sciences
3 publications, 27.27%
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Molecules
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1 publication, 9.09%
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New Journal of Chemistry
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1 publication, 9.09%
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Microchemical Journal
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Microchemical Journal
1 publication, 9.09%
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Phosphorus, Sulfur and Silicon and the Related Elements
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1 publication, 9.09%
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1 publication, 9.09%
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Biomolecules
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1 publication, 9.09%
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Results in Chemistry
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1 publication, 9.09%
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Russian Chemical Reviews
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Russian Chemical Reviews
1 publication, 9.09%
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Citations by publishers
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
6 publications, 54.55%
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Elsevier
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Elsevier
2 publications, 18.18%
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
1 publication, 9.09%
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Taylor & Francis
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Taylor & Francis
1 publication, 9.09%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 9.09%
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Novotortsev V. K. et al. Dispirooxindoles based on 2-selenoxo-imidazolidin-4-ones: Synthesis, cytotoxicity and ros generation ability // International Journal of Molecular Sciences. 2021. Vol. 22. No. 5. pp. 1-26.
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Novotortsev V. K., Kukushkin M. E., Tafeenko V. A., Skvortsov D. A., Kalinina M. A., Timoshenko R. V., Chmelyuk N. S., Vasilyeva L. A., Tarasevich B. N., Gorelkin P., Erofeev A. S., Majouga A. G., Zyk N. V., Beloglazkina E. K. Dispirooxindoles based on 2-selenoxo-imidazolidin-4-ones: Synthesis, cytotoxicity and ros generation ability // International Journal of Molecular Sciences. 2021. Vol. 22. No. 5. pp. 1-26.
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TY - JOUR
DO - 10.3390/ijms22052613
UR - https://doi.org/10.3390%2Fijms22052613
TI - Dispirooxindoles based on 2-selenoxo-imidazolidin-4-ones: Synthesis, cytotoxicity and ros generation ability
T2 - International Journal of Molecular Sciences
AU - Novotortsev, Vladimir K
AU - Kukushkin, Maxim E.
AU - Tafeenko, Viktor A.
AU - Skvortsov, Dmitry A.
AU - Timoshenko, Roman V
AU - Chmelyuk, Nelly S.
AU - Vasilyeva, Liliya A
AU - Tarasevich, Boris N
AU - Erofeev, Alexander S.
AU - Majouga, Alexander G.
AU - Zyk, Nikolai V.
AU - Kalinina, Marina A
AU - Gorelkin, Peter
AU - Beloglazkina, Elena K.
PY - 2021
DA - 2021/03/05 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 1-26
IS - 5
VL - 22
PMID - 33807662
SN - 1661-6596
SN - 1422-0067
ER -
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@article{2021_Novotortsev,
author = {Vladimir K Novotortsev and Maxim E. Kukushkin and Viktor A. Tafeenko and Dmitry A. Skvortsov and Roman V Timoshenko and Nelly S. Chmelyuk and Liliya A Vasilyeva and Boris N Tarasevich and Alexander S. Erofeev and Alexander G. Majouga and Nikolai V. Zyk and Marina A Kalinina and Peter Gorelkin and Elena K. Beloglazkina},
title = {Dispirooxindoles based on 2-selenoxo-imidazolidin-4-ones: Synthesis, cytotoxicity and ros generation ability},
journal = {International Journal of Molecular Sciences},
year = {2021},
volume = {22},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {mar},
url = {https://doi.org/10.3390%2Fijms22052613},
number = {5},
pages = {1--26},
doi = {10.3390/ijms22052613}
}
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MLA
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Novotortsev, Vladimir K., et al. “Dispirooxindoles based on 2-selenoxo-imidazolidin-4-ones: Synthesis, cytotoxicity and ros generation ability.” International Journal of Molecular Sciences, vol. 22, no. 5, Mar. 2021, pp. 1-26. https://doi.org/10.3390%2Fijms22052613.