Taran S. Synthesis and Research of the Biologically Active Derivatives of 2-oxo-4-hydroxyquinoline

The thesis is devoted to the development of new promising scientific approach in the synthesis of BAS on the basis of quinoline derivatives. An original universal method for obtaining 3-substituted 2-oxo-4-hydroxyquinolines has been proposed. It has been successfully used for the synthesis of 3-alkyl-, 3-acylamino derivatives and the corresponding quinolin-3-acetic (propionic) acids. By the preparative methods developed 3-heteryl-, 3-brom-1-R-2-oxo-4-hydroxyquinolines, 1-R-2-oxo-3,4-dihydroxyquinolines, 2-alkyl(aryl)-5H-oxazolo[4,5-c]quinolin-4-ones, esters and amides of 1-R-2-oxo-4-hydroxyquinolin-3-carboxylic and 3-acetic acids have been also synthesized. The possible mechanisms of the chemical changes given have been considered. The possibility of performing condensation by Dickman type without involving the basic catalysts has been proven experimentally and substantiated theoretically. It has been found that the chemical lability of 3-amino substituted 2-oxo-4-hydroxyquinolines is connected with their transformation in symmetric diquinolines under the influence of UV-radiation. The structure of the compounds obtained has been confirmed by the modern methods of instrumental analysis (Including X-ray diffraction method). As a result of the biological studies the compounds with a marked antithyroid, antimicrobial, local anesthetic, membrane-stabilizing, anticoagulant and fungicidal activity have been revealed. The normative technical documentation for a promising thyreostatic "Thyreochine" has been elaborated and tested in the conditions of the production