European Journal of Medicinal Chemistry, volume 140, pages 141-154
Synthesis and biological evaluation of new substituted thioglycolurils, their analogues and derivatives
Anikina Lada V
2
,
Nechaeva Tatyana V
3, 4
,
Pukhov Sergey
2
,
Karpova Tatyana B
1
,
Popkov Sergey V
5
,
Nelyubina Yulia V.
6, 7, 8
,
Kolotyrkina Natalya G
1
,
7
RUSSIAN ACADEMY OF SCIENCES
8
Moscow 119991 Russian Federation
|
Publication type: Journal Article
Publication date: 2017-11-01
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 6.7
ISSN: 02235234, 17683254
Organic Chemistry
Drug Discovery
General Medicine
Pharmacology
Abstract
A novel series of substituted N-aminothioglycolurils was synthesized by tandem hydrazone formation - ring contraction reaction of 3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-6-ones with (E)-3-phenyl(furan-2-yl)acrylaldehyde derivatives. S-Alkyl substituted N-aminothioglycolurils were prepared through alkylation of corresponding thioglycolurils with iodoalkane or 4-chlorobenzylchloride. Methylthio group in S-methyl derivatives can be substituted with hydroxyl group in acid medium to give N-aminoglycolurils. Representative compounds were evaluated for their cytotoxic activity against RD, A549, HCT116 and MCF7 human cancer cell lines by MTT-assay and screened for their antifungal activity against phytopathogenic fungi using the mycelium growth inhibition method in vitro. Among the derivatives, 4-((E)-((E)-3-(2-Methoxyphenyl)allylidene)amino)-3-methyl-1-phenylthioglycoluril 8i was found to have the highest antiproliferative activity toward the RD and HCT116 cell lines (8i: IC50 = 0.02 and 0.012 μM, respectively), which exceeded cytotoxicity of reference drugs. 1,3-Diethyl-4-((E)-((E)-3-(2-methoxyphenyl)allylidene)amino)thioglycoluril 8l showed the most marked activity toward A549 cells (8l: IC50 = 0.61 μM) compared to reference drugs. The IC50 values of thioglycolurils 8i,l against normal human embryonic kidney cells HEK293 were 0.23 and 86.11 μM, respectively, exceeding the IC50 values of this compound toward the RD, HCT116 (8i) and A549 cells (8l) by one-two orders of magnitude. Experiments with annexin showed that compounds 8b,i,l induced apoptosis in Jurkat cells (acute T cell leukemia). Alkylthioderivatives 12a,13a displayed the strongest antifungal action against R. solani, F. oxysporum, and F. moniliforme exceeding those of triadimefon.
Citations by journals
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Russian Chemical Bulletin
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6 publications, 22.22%
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1 publication, 3.7%
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1 publication, 3.7%
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1 publication, 3.7%
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1 publication, 3.7%
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Russian Journal of General Chemistry
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1 publication, 3.7%
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Citations by publishers
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Springer Nature
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Springer Nature
9 publications, 33.33%
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Elsevier
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3 publications, 11.11%
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3 publications, 11.11%
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Thieme
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2 publications, 7.41%
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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
2 publications, 7.41%
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Wiley
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Wiley
1 publication, 3.7%
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Bentham Science
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Bentham Science
1 publication, 3.7%
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Taylor & Francis
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Taylor & Francis
1 publication, 3.7%
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Pleiades Publishing
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Pleiades Publishing
1 publication, 3.7%
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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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Gazieva G. A. et al. Synthesis and biological evaluation of new substituted thioglycolurils, their analogues and derivatives // European Journal of Medicinal Chemistry. 2017. Vol. 140. pp. 141-154.
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Gazieva G. A., Anikina L. V., Nechaeva T. V., Pukhov S., Karpova T. B., Popkov S. V., Nelyubina Y. V., Kolotyrkina N. G., Kravchenko A. N. Synthesis and biological evaluation of new substituted thioglycolurils, their analogues and derivatives // European Journal of Medicinal Chemistry. 2017. Vol. 140. pp. 141-154.
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TY - JOUR
DO - 10.1016/j.ejmech.2017.09.009
UR - https://doi.org/10.1016%2Fj.ejmech.2017.09.009
TI - Synthesis and biological evaluation of new substituted thioglycolurils, their analogues and derivatives
T2 - European Journal of Medicinal Chemistry
AU - Gazieva, Galina A.
AU - Anikina, Lada V
AU - Nechaeva, Tatyana V
AU - Karpova, Tatyana B
AU - Popkov, Sergey V
AU - Kolotyrkina, Natalya G
AU - Kravchenko, Angelina N.
AU - Pukhov, Sergey
AU - Nelyubina, Yulia V.
PY - 2017
DA - 2017/11/01 00:00:00
PB - Elsevier
SP - 141-154
VL - 140
SN - 0223-5234
SN - 1768-3254
ER -
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@article{2017_Gazieva,
author = {Galina A. Gazieva and Lada V Anikina and Tatyana V Nechaeva and Tatyana B Karpova and Sergey V Popkov and Natalya G Kolotyrkina and Angelina N. Kravchenko and Sergey Pukhov and Yulia V. Nelyubina},
title = {Synthesis and biological evaluation of new substituted thioglycolurils, their analogues and derivatives},
journal = {European Journal of Medicinal Chemistry},
year = {2017},
volume = {140},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016%2Fj.ejmech.2017.09.009},
pages = {141--154},
doi = {10.1016/j.ejmech.2017.09.009}
}