Molecular Diversity, volume 22, issue 3, pages 585-599
The influence of substituents on the reactivity and cytotoxicity of imidazothiazolotriazinones
Gazieva Galina A
1
,
Izmestev Alexei N
1
,
Anikina Lada V
2
,
Pukhov Sergey A.
2
,
Meshchaneva Marina E
1, 3
,
Khakimov Dmitry V.
1, 4
,
Kolotyrkina Natalya G
1
,
Publication type: Journal Article
Publication date: 2018-03-14
Journal:
Molecular Diversity
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 3.8
ISSN: 13811991, 1573501X
Catalysis
Organic Chemistry
Drug Discovery
Inorganic Chemistry
Physical and Theoretical Chemistry
Molecular Biology
General Medicine
Information Systems
Abstract
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
Citations by journals
|
1
2
3
|
|
|
New Journal of Chemistry
|
New Journal of Chemistry
3 publications, 15.79%
|
|
Organic and Biomolecular Chemistry
|
Organic and Biomolecular Chemistry
2 publications, 10.53%
|
|
ChemistrySelect
|
ChemistrySelect
2 publications, 10.53%
|
|
Chemistry of Heterocyclic Compounds
|
Chemistry of Heterocyclic Compounds
2 publications, 10.53%
|
|
Beilstein Journal of Organic Chemistry
|
Beilstein Journal of Organic Chemistry
1 publication, 5.26%
|
|
Organic Chemistry Frontiers
|
Organic Chemistry Frontiers
1 publication, 5.26%
|
|
Mendeleev Communications
|
Mendeleev Communications
1 publication, 5.26%
|
|
International Journal of Molecular Sciences
|
International Journal of Molecular Sciences
1 publication, 5.26%
|
|
Molecular Diversity
|
Molecular Diversity
1 publication, 5.26%
|
|
Russian Chemical Reviews
|
Russian Chemical Reviews
1 publication, 5.26%
|
|
Postepy Higieny i Medycyny Doswiadczalnej
|
Postepy Higieny i Medycyny Doswiadczalnej, 1, 5.26%
Postepy Higieny i Medycyny Doswiadczalnej
1 publication, 5.26%
|
|
Archiv der Pharmazie
|
Archiv der Pharmazie
1 publication, 5.26%
|
|
RSC Medicinal Chemistry
|
RSC Medicinal Chemistry
1 publication, 5.26%
|
|
1
2
3
|
Citations by publishers
|
1
2
3
4
5
6
7
|
|
|
Royal Society of Chemistry (RSC)
|
Royal Society of Chemistry (RSC)
7 publications, 36.84%
|
|
Wiley
|
Wiley
3 publications, 15.79%
|
|
Springer Nature
|
Springer Nature
3 publications, 15.79%
|
|
Beilstein-Institut
|
Beilstein-Institut
1 publication, 5.26%
|
|
Elsevier
|
Elsevier
1 publication, 5.26%
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
|
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 5.26%
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 5.26%
|
|
Index Copernicus International
|
Index Copernicus International, 1, 5.26%
Index Copernicus International
1 publication, 5.26%
|
|
1
2
3
4
5
6
7
|
- 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.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2019,2020,2021,2022,2023,2024],"ids":[0,0,0,0,0,0],"codes":[0,0,0,0,0,0],"imageUrls":["","","","","",""],"datasets":[{"label":"Citations number","data":[3,2,3,9,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["15.79","10.53","15.79","47.37","5.26","5.26"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["New Journal of Chemistry","Organic and Biomolecular Chemistry","ChemistrySelect","Chemistry of Heterocyclic Compounds","Beilstein Journal of Organic Chemistry","Organic Chemistry Frontiers","Mendeleev Communications","International Journal of Molecular Sciences","Molecular Diversity","Russian Chemical Reviews","Postepy Higieny i Medycyny Doswiadczalnej","Archiv der Pharmazie","RSC Medicinal Chemistry"],"ids":[1404,541,8021,16828,21928,3991,5294,14627,9362,23802,2652,15226,26876],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/ex6KJoZujZOZFZh7jGfeHauiftuB3CI7iwJVFRDg_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp"],"datasets":[{"label":"","data":[3,2,2,2,1,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[15.79,10.53,10.53,10.53,5.26,5.26,5.26,5.26,5.26,5.26,5.26,5.26,5.26],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Royal Society of Chemistry (RSC)","Wiley","Springer Nature","Beilstein-Institut","Elsevier","Multidisciplinary Digital Publishing Institute (MDPI)","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii","Index Copernicus International"],"ids":[123,11,8,6139,17,202,9422,1014],"codes":[0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/ex6KJoZujZOZFZh7jGfeHauiftuB3CI7iwJVFRDg_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp",""],"datasets":[{"label":"","data":[7,3,3,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[36.84,15.79,15.79,5.26,5.26,5.26,5.26,5.26],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Gazieva G. A. et al. The influence of substituents on the reactivity and cytotoxicity of imidazothiazolotriazinones // Molecular Diversity. 2018. Vol. 22. No. 3. pp. 585-599.
GOST all authors (up to 50)
Copy
Gazieva G. A., Izmestev A. N., Anikina L. V., Pukhov S. A., Meshchaneva M. E., Khakimov D. V., Kolotyrkina N. G., Kravchenko A. N. The influence of substituents on the reactivity and cytotoxicity of imidazothiazolotriazinones // Molecular Diversity. 2018. Vol. 22. No. 3. pp. 585-599.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1007/S11030-018-9813-8
UR - https://doi.org/10.1007%2FS11030-018-9813-8
TI - The influence of substituents on the reactivity and cytotoxicity of imidazothiazolotriazinones
T2 - Molecular Diversity
AU - Izmestev, Alexei N
AU - Anikina, Lada V
AU - Pukhov, Sergey A.
AU - Meshchaneva, Marina E
AU - Khakimov, Dmitry V.
AU - Kolotyrkina, Natalya G
AU - Gazieva, Galina A
AU - Kravchenko, Angelina N
PY - 2018
DA - 2018/03/14 00:00:00
PB - Springer Nature
SP - 585-599
IS - 3
VL - 22
SN - 1381-1991
SN - 1573-501X
ER -
Cite this
BibTex
Copy
@article{2018_Gazieva,
author = {Alexei N Izmestev and Lada V Anikina and Sergey A. Pukhov and Marina E Meshchaneva and Dmitry V. Khakimov and Natalya G Kolotyrkina and Galina A Gazieva and Angelina N Kravchenko},
title = {The influence of substituents on the reactivity and cytotoxicity of imidazothiazolotriazinones},
journal = {Molecular Diversity},
year = {2018},
volume = {22},
publisher = {Springer Nature},
month = {mar},
url = {https://doi.org/10.1007%2FS11030-018-9813-8},
number = {3},
pages = {585--599},
doi = {10.1007/S11030-018-9813-8}
}
Cite this
MLA
Copy
Gazieva, Galina A., et al. “The influence of substituents on the reactivity and cytotoxicity of imidazothiazolotriazinones.” Molecular Diversity, vol. 22, no. 3, Mar. 2018, pp. 585-599. https://doi.org/10.1007%2FS11030-018-9813-8.