The influence of substituents on the reactivity and cytotoxicity of imidazothiazolotriazinones

Gazieva G.A., Izmest’ev A.N., Anikina L.V., Pukhov S.A., Meshchaneva M.E., Khakimov D.V., Kolotyrkina N.G., Kravchenko A.N.
Тип документаJournal Article
Дата публикации2018-04-25
Название журналаMolecular Diversity
ИздательSpringer Nature
КвартильQ2
ISSN13811991, 1573501X
  • Catalysis
  • Organic Chemistry
  • Drug Discovery
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Molecular Biology
  • General Medicine
  • Information Systems
Краткое описание
A series of tetrahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7(1H, 6H)-diones were synthesized via the reaction of imidazotriazinethiones and bromoacetic acid followed by condensation with isatins. Amidine skeletal rearrangement of 3,3a,9,9a-tetrahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7 (1H, 6H)-diones into 1,3a,4,9a-tetrahydroimidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine-2,8 (3H, 7H)-diones under KOH treatment has been studied. The influence of substituents at positions 1,3,3a,6,9a of imidazothiazolotriazine on the ability to undergo rearrangement was analyzed based on experimental data and theoretical calculations. Both imidazothiazolo[3,2-b]triazines and their rearrangement products were evaluated for their cytotoxic activity against rhabdomyosarcoma, A549, HCT116 and MCF7 human cancer cell lines by MTT assay. Among the derivatives, 1,3-diethyl-6-[1-(2-propyl)-2-oxoindolin-3-ylidene]-3,3a,9,9a-tetrahydroimidazo [4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7(1H, 6H)-dione 4i was found to have the highest antiproliferative activity toward the tested cell lines (4i: $$\hbox {IC}_{50} = 2.20$$IC50=2.20, 2.29, 0.47 and $$3.11\,{\upmu }\hbox {M}$$3.11μM, respectively). The $$\hbox {IC}_{50}$$IC50 value of compound 4i against normal human embryonic kidney cells HEK293 was $$19.34\,{\upmu }\hbox {M}$$19.34μM, which appeared to be 6–41-fold higher than $$\hbox {IC}_{50}$$IC50 values of 4i against human cancer cells.Graphical Abstract
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1. Gazieva G.A. и др. The influence of substituents on the reactivity and cytotoxicity of imidazothiazolotriazinones // Molecular Diversity. 2018. Т. 22. № 3. С. 585–599.
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TY - JOUR

DO - 10.1007/s11030-018-9813-8

UR - http://dx.doi.org/10.1007/S11030-018-9813-8

TI - The influence of substituents on the reactivity and cytotoxicity of imidazothiazolotriazinones

T2 - Molecular Diversity

AU - Gazieva, Galina A.

AU - Izmest’ev, Alexei N.

AU - Anikina, Lada V.

AU - Pukhov, Sergey A.

AU - Meshchaneva, Marina E.

AU - Khakimov, Dmitry V.

AU - Kolotyrkina, Natalya G.

AU - Kravchenko, Angelina N.

PY - 2018

DA - 2018/03/14

PB - Springer Science and Business Media LLC

SP - 585-599

IS - 3

VL - 22

SN - 1381-1991

SN - 1573-501X

ER -

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@article{2018,

doi = {10.1007/s11030-018-9813-8},

url = {https://doi.org/10.1007%2Fs11030-018-9813-8},

year = 2018,

month = {mar},

publisher = {Springer Science and Business Media {LLC}},

volume = {22},

number = {3},

pages = {585--599},

author = {Galina A. Gazieva and Alexei N. Izmest'ev and Lada V. Anikina and Sergey A. Pukhov and Marina E. Meshchaneva and Dmitry V. Khakimov and Natalya G. Kolotyrkina and Angelina N. Kravchenko},

title = {The influence of substituents on the reactivity and cytotoxicity of imidazothiazolotriazinones}

}

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Gazieva, Galina A. et al. “The Influence of Substituents on the Reactivity and Cytotoxicity of Imidazothiazolotriazinones.” Molecular Diversity 22.3 (2018): 585–599. Crossref. Web.