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Spiro- and dispiro-conjugated heterocycles containing pharmacophore indolinone 2-chalcogenimidazolones fragments demon- strated high antitumor activity, which is usually associated with their limited conformational mobility, allowing them to maintain the spatial position of important substituents required for interaction with biotargets, and the ability of the indolinone fragment to act as inhibitors of BECN1, AKT1 kinase, and p53-MDM2 protein-protein interaction. We have shown the possibility to use 1,3-dipolar cycloaddition reactions of nitrogen-containing 1,3-dipoles of various structural types (azomethine ylides, nitrile oxides, nitrilimines) for the regio- and stereoselective synthesis of five-membered nitrogen-containing heterocycles, spiro-linked with imidazolone and indolinone fragments.