Synthesis and anti-mitotic activity of 6,7-dihydro-4H-isothiazolo[4,5-b]pyridin-5-ones: In vivo and cell-based studies
Victor Semenov
1
,
Boris Lichitsky
1
,
Arkady A. Dudinov
1
,
Mikhail M. Krayushkin
1
,
Leonid D Konyushkin
1
,
Olga P Atamanenko
1
,
Irina B Karmanova
1
,
Yuri A. Strelenko
1
,
Boris Shor
2
,
Marina Semenova
3
,
Alex S. Kiselyov
4
2
Immune Pharmaceuticals LLC, 430 East 29th Street, Suite 940, New York, NY, 10016, USA
|
Publication type: Journal Article
Publication date: 2017-01-01
scimago Q1
wos Q1
SJR: 1.142
CiteScore: 11.3
Impact factor: 5.9
ISSN: 02235234, 17683254
PubMed ID:
27718473
Organic Chemistry
Drug Discovery
General Medicine
Pharmacology
Abstract
A series of 3,7-diaryl-6,7-dihydroisothiazolo [4,5-b]pyridin-5(4H)-ones 8 and 9 was synthesized by multicomponent condensation of 3-aryl-5-isothiazolecarboxylic acid esters 4a-f with aromatic (or thienyl) aldehydes 7 and Meldrum's acid in an acidic medium. The targeted compounds were evaluated for their antimitotic microtubule destabilizing activity using in vivo phenotypic sea urchin embryo model and in vitro human cancer cell-based assays. Selected dihydroisothiazolopyridinones altered sea urchin egg cleavage in 2-10 nM concentrations together with significant cytotoxicity against cancer cells including chemoresistant cell lines (IC50 in submicromolar - low nanomolar concentration range). Both approaches confirmed antimitotic microtubule destabilizing mechanism of action of the izothiazole derivatives. Structure-activity relationship study determined the importance of p-methoxybenzene A-ring for the antiproliferative effect. The most potent compound 9b containing p-methoxybenzene A-ring and thiophene B-ring caused mitotic arrest and disintegration of cell microtubules.
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Semenov V. et al. Synthesis and anti-mitotic activity of 6,7-dihydro-4H-isothiazolo[4,5-b]pyridin-5-ones: In vivo and cell-based studies // European Journal of Medicinal Chemistry. 2017. Vol. 125. pp. 573-585.
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Semenov V., Lichitsky B., Komogortsev A., Dudinov A. A., Krayushkin M. M., Konyushkin L. D., Atamanenko O. P., Karmanova I. B., Strelenko Y. A., Shor B., Semenova M., Kiselyov A. S. Synthesis and anti-mitotic activity of 6,7-dihydro-4H-isothiazolo[4,5-b]pyridin-5-ones: In vivo and cell-based studies // European Journal of Medicinal Chemistry. 2017. Vol. 125. pp. 573-585.
Cite this
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TY - JOUR
DO - 10.1016/j.ejmech.2016.09.075
UR - https://doi.org/10.1016/j.ejmech.2016.09.075
TI - Synthesis and anti-mitotic activity of 6,7-dihydro-4H-isothiazolo[4,5-b]pyridin-5-ones: In vivo and cell-based studies
T2 - European Journal of Medicinal Chemistry
AU - Semenov, Victor
AU - Lichitsky, Boris
AU - Komogortsev, Andrey
AU - Dudinov, Arkady A.
AU - Krayushkin, Mikhail M.
AU - Konyushkin, Leonid D
AU - Atamanenko, Olga P
AU - Karmanova, Irina B
AU - Strelenko, Yuri A.
AU - Shor, Boris
AU - Semenova, Marina
AU - Kiselyov, Alex S.
PY - 2017
DA - 2017/01/01
PB - Elsevier
SP - 573-585
VL - 125
PMID - 27718473
SN - 0223-5234
SN - 1768-3254
ER -
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BibTex (up to 50 authors)
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@article{2017_Semenov,
author = {Victor Semenov and Boris Lichitsky and Andrey Komogortsev and Arkady A. Dudinov and Mikhail M. Krayushkin and Leonid D Konyushkin and Olga P Atamanenko and Irina B Karmanova and Yuri A. Strelenko and Boris Shor and Marina Semenova and Alex S. Kiselyov},
title = {Synthesis and anti-mitotic activity of 6,7-dihydro-4H-isothiazolo[4,5-b]pyridin-5-ones: In vivo and cell-based studies},
journal = {European Journal of Medicinal Chemistry},
year = {2017},
volume = {125},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/j.ejmech.2016.09.075},
pages = {573--585},
doi = {10.1016/j.ejmech.2016.09.075}
}
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