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The significant interest in the search and study of antioxidants, both natural and synthetic, is explained by the possibility of preventing these harmful effects of free radicals in the human body. The similarity of macroheterocyclic derivatives to endogenous biomolecules makes them promising for research as antioxidant agents. By the interaction of 1,3-oxoheterocycloalkanes with ethyl 2-diazo-3-oxobutanoate, previously unexplored polyfunctional oxygen and sulfur-containing macroheterocycles are obtained. The relative antioxidant activity of new macroheterocycles in two model systems: generating active forms of oxygen and modulating lipid peroxidation reaction, was revealed active forms of oxygen and described by the method of recording luminol-dependent chemiluminescence lipid peroxidation reaction. The in vitro cytotoxic activity of the studied compounds was studied on Jurkat (human T-lymphoblastic leukemia cells), HepG2 (human liver carcinoma cells), HEK293 (human embryonic kidney cells) cell lines. The data obtained indicate practical significance. So, reagents 1-7 in the active forms of oxygen generating system have anti- and prooxidative properties, and in the system modeling lipid peroxidation reaction, they show only prooxidant activity. The influence of heterocycles 1–7 on the processes of free radical oxidation was determined by the intensity of the maximum flash (Imax, у.е.) and the luminosity of light (S, у.е.). Compounds with maximum anti- (4) and prooxidative (6) properties in the active forms of oxygen generating system and reagent 3 with the highest prooxidant activity in the lipid peroxidation reaction modeling system do not possess cytotoxic activity in vitro on cell lines HEK293 and HepG2 cultured in DMEM medium (Biolot, Russia), Jurkat in RPMI medium (Biolot, Russia) in the presence of 10% fetal calf serum (Invitrogen, USA), 2 mM L-glutamine and 50 μg / ml gentamicin sulfate.

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