Synthesis and antiproliferative activity characterization of new imidazothiazolotriazine oxindolylidene derivatives containing various substituents in the oxindole ring

Condensation of 1,3-diethyltetrahydroimidazo[4,5- е ]thiazolo[3,2- b ][1,2,4]triazine-2,7-dione with isatins followed by framework rearrangement in the thiazolotriazine moiety was used to synthesize two new series of oxindolylidenetetrahydroimidazo[4,5- е ]thiazolo- [3,2- b ][1,2,4]triazine-2,7-dion...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2022-09, Vol.58 (10), p.531-538
Main Authors: Izmest’ev, Alexei N., Kravchenko, Angelina N., Gazieva, Galina A.
Format: Article
Language:English
Subjects:
Antiproliferatives
Cell death
Central nervous system
Chemistry
Chemistry and Materials Science
Diketones
Heterocyclic compounds
Melanoma
Organic Chemistry
Pharmacy
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Summary:Condensation of 1,3-diethyltetrahydroimidazo[4,5- е ]thiazolo[3,2- b ][1,2,4]triazine-2,7-dione with isatins followed by framework rearrangement in the thiazolotriazine moiety was used to synthesize two new series of oxindolylidenetetrahydroimidazo[4,5- е ]thiazolo- [3,2- b ][1,2,4]triazine-2,7-diones and oxindolylidenetetrahydroimidazo[4,5- е ]thiazolo[2,3- c ][1,2,4]triazine-2,8-diones containing various substituents in the oxindole moiety. The obtained compounds were tested for antiproliferative activity. The greatest activity was observed in the case of 1-alkyl-7-methyloxindolylidene derivatives of imidazo[4,5- е ]thiazolo[2,3- c ]triazine, which not only inhibited the growth of more than half of the studied cell lines, but also caused cell death in the SF-539 cell line (central nervous system cancer, mean growth percent –7.82%) and MDA-MB-435 (melanoma, –30.97 and –13.64%).
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-022-03125-3