SYNTHESIS AND BIOLOGICAL ACTIVITY STUDY OF POLYCYCLIC 1-THIOXO-9,10a-DIHYDROPYRROLO[3,4-b]CARBAZOLE-3,10-DIONES
DOI:
https://doi.org/10.11603/2312-0967.2020.4.11641Keywords:
organic synthesis, indole, thiohydantoin, antitumor activityAbstract
The aim of the work. Design and synthesis of novel fused compounds based on indole and thiohydantoin (2-thioxoimidazolin-4-one) cycles as potential drug-like molecules. Study of their antitumor activity.
Materials and Methods. Organic synthesis, NMR spectroscopy, pharmacological screening.
Results and Discussion. Condensed tetracyclic 1-thioxo-9,10a-dihydropyrrolo[3,4-b]carbazole-3,10-diones were synthesized in the reaction of 3-(4-oxo-2-thioxothiazolidin-5-ylidenemethylene)-1H-indole-carboxylic acids with thiohydantoin in acetic acid under reflux. The reaction of 3-formylindoline-2-carboxylate with 2-thiohydantoin yielded 5-fluoro-3-(4-oxo-2-thioxoimidazolidin-5-ylidenemethyl)-1H-indole-2-carboxylate methyl ester. The antiproliferative activity of the synthesized compounds was studied at a concentration of 10-5 M on a panel of cancer cells.
Conclusions. An effective method for the synthesis of 1-thioxo-9,10a-dihydropyrrolo[3,4-b]carbazole-3,10-diones has been developed. A moderate effect of the synthesized compounds on the UO-31 renal cancer line has been established.
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