Polvkovych S. Design of condensed heterocyclic systems based on 1,4-quinones, quinoxalines and 1,3,5-triazines

The dissertation is devoted to the development of search strategy of the directions of using reactions of nucleophilic substitution, cyclocondensation and cycloaddition for the design of new nitrogen- and sulfur-containing heterocycles based on quinone, quinoxaline and 1,3,5-triazine derivatives. Condensed derivatives based on 5-substituted derivatives of 2,3-dichloro-1,4-naphthoquinone have been obtained by the reaction with aminothiotriazoles. It has been found that the obtained derivatives are susceptible to intramolecular cyclocondensation with the formation of heterocyclic systems containing the thiadiazin and semiquinoid fragments. The nucleophilic substitution reaction between benzenthiosulfoacids and halogen derivatives of quinones and quinoxalines has been studied. A numder of 5-substituted carbazolediones have been synthesized by the Buchwald-Hartwig reaction. A series of new polycarbocyclic 1,4-dihydroanthracene-9,10-diones by the Diels-Alder reaction have been obtained. A number of polyheterocyclic derivatives based on azo-bis-cyanuric chloride have been synthesized using a direct and inverse hetero-Diels-Alder reaction. It has been revealed that interaction between azo-bis-cyanuric chloride and furan and styrene occurs with formation of the product of inverse Diels-Alder reaction through the stage of sigmatropic rearrangement. Formation of the products of interaction between azo-bis-cyanuric chloride and vinyl derivatives passes through the mechanism of inverse reaction in one stage. Reaction between azo-bic- cyanuric chloride and cyclohexadiene goes with forming the product of carboline structure (E)-6,6'-(1-(hexa-2,5-diene-1-yl)-hydrazine-1,2-diyl)bis(2,4-dichlor-1,3,5-triazine). Heterocyclic quinones with a strictly defined geometry have been obtained by the reaction of 1,3-dipolar cycloaddition. The in silico and in vitro studies of biological activity of the synthesized compounds have been carried out, antimicrobial, antitumor and antithrombotic activity of the compounds have been tested and the effect of the obtained substances on tyrosine protein kinase has been determined.