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

Alexei N Izmest'ev; Angelina N Kravchenko; Galina A Gazieva

doi:10.1007/s10593-022-03125-3

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

Chem Heterocycl Compd (N Y). 2022;58(10):531-538. doi: 10.1007/s10593-022-03125-3. Epub 2022 Oct 29.

Authors

Alexei N Izmest'ev^{1

2}, Angelina N Kravchenko¹, Galina A Gazieva¹

Affiliations

¹ N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave, Moscow, 119991 Russia.
² National University of Science and Technology "MISiS", 4 Leninsky Ave, Moscow, 119049 Russia.

Abstract

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%).

Supplementary information: The online version contains supplementary material available at 10.1007/s10593-022-03125-3.

Keywords: antiproliferative activity; condensation; imidazothiazolotriazines; isatins; rearrangement.

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