Harkov S. Synthesis and biological activity of thiazolidine derivatives with 2-oxo-1,3-dihydroindole fragment in molecules

Object - N- and S- alkylation reactions, heterocyclisation, hydrazinolysis, Knoevenagel condensation; the purpose - the search of new potential biologically active substances as potential drugs, among synthesized 2-oxo-1,3-dihydroindole substituted 4- thiazolidinones; methods - organic synthesis, pharmacological screening, molecular docking, NMR and IR spectroscopy, gas chromatography, mass spectrometry, COMPARE analysis; novelty - developed synthesis methods, not described in the literature, of 5 - (2 -oxo -1,3- dihydroindole)-substituted 4-thiazolidinone and thiazolidinone-triazinoindoles; the interaction of 5-R-isatins and 2-chloro-N-aryl(heteryl)acetamides via N-alkylation reaction resulted in the isatin derivatives obtaining new heterocyclic formations, which combined indole molecule and thiazole, triazole or pyrazoline heterocycles; the 4-thiazolidinones and the synthesized 2-(2,3-dioxo-1,3-dihydroindole-1-yl)-N-aryl(heteryl)acetimides via Knoevenagel condensation, a new series of 5-istainylidenesubstitued compounds were obtained; 2-{3-[3-alyl-(2-arylimino)-4-oxothiazolidine-5-ylidene]-2-oxo-1,3-dihydroindole-1-yl}-N-arylacetimides were synthesized via one-pot three-component reaction and an alternative approach to the synthesis of new indolinsubstitued 4-thiazolidinones and 4-(2-oxo-1,3-dihydroindole-3-ylidenemehtyl)-aryl-(2,4-dioxothizolidine-5-yl)-acetates, based on the condensation reaction of 4-thiazolidinonesubstitued benzaldehydes and methylactive 1,3-dihydroindole-2-ones; a series of potential biologically active 3-triazinoindole- and 2-thiadiazinidolesubstitued 4-thiazolidinones were for the first time obtained on the base of 5-R-isatines like starting compounds; there were synthesized 99 compounds (79 - for the first time); low-toxic compounds were identified, from which 4 compounds with antitumor activity, 6 compounds with antiviral activity and selective influence to some influenza viruses and 3 compounds with antioxidant activity; based on analysis of correlation "structure - action" and the results of in silico studies the recommendation for rational design of potential anticancer and antiviral agents were proposed; introduced into scientific and educational process of National University "Lviv Politechnic", National Pharmaceutical University and Zaporizhzhya State Medical University; area - pharmacy.