Turov K. Synthesis and Prorerties of new di- and trifunctionally substituted 1,3-thiazoles

Di-, and trifunctionalized 1,3-thiazole. The purpose of this work was in synthesis of electronicpure 1,3-thiazole and the study of their interactions with amines, thiols, phenols and stabilized ylides, which would lead to the synthesis of a number of previously unknown di-and tri-substituted thiazole with pharmacophore groups and search among them bioregulators different actions. Chemical Synthesis, IR and NMR spectroscopy (proof structures synthesized compounds), mass spectrometry (determination of the mass of the molecular ions of some of the synthesized compounds), X-ray diffraction studies (one to establish the structure of some of the new compounds.) The interaction of 1-tosyl-2,2-dichloroenamides with Lowesson reagent, which leads to the formation of 4-tosyl-1,3-thiazole, containing in position C5 mobile chlorine atom, which was used for the synthesis of previously unknown 4, 5 difuctionalized -thiazole. Analogue of these substrates - 4-tosyl-2-phenyl-5- (4-chlorophenyl)sulfonyl-1,3-thiazol - reacts with a "soft" and "hard" nucleophiles in different ways: with, respectively, the center of C4 or C5, which is probably due to the principle of "symbiosis" in transition state. Shown that the nucleophilic agents, regardless of their nature, the first attack C2 center, later S-nucleophiles interact with the center C5, and O-and N-nucleophiles - centered C4 thiazole ring. Found that 2-hydrazine-4-tosyl-5-chloro-1,3-thiazole, which is obtained by reacting 1-tosyl-2 ,2-dichlorethenylisothiocianate with hydrazine hydrate, mixed react with thiols and amines. The direction of its interaction with nucleophiles greatly depends on the nature of the latter, which was used in the regioselective synthesis of previously unknown number trifunktsionalnozamischenih thiazole. Among the synthesized compounds were found substances with antioxidant properties and are affecting the livelihoods of the yeast cells. Some thiazole derivatives with piperazine moiety in position C5 were effective antitumor agents that stimulate interest in a deeper study them. Sphere of the use is bioorganic chemistry.