Kornii Y. Synthesis of new iminohydantoin derivatives with antiviral and anticancer activity

Iminohydantoins with antiviral and anticancer activity, 3-trifluoromethyldiazerins. Development of new approaches to the synthesis of various iminohydantoin derivatives, mainly with pharmacophore sulfamide groups, including amino acid fragments and trifluoromethyldiazirine, directions of their cyclization. Develop preparative techniques and synthesize cyclic aliphatic secondary amines with trifluoromethyldiazirine substituent and use them to produce hydantoin sulfamides. Investigate the interaction of 2-amino-3,3-dichloroacrylonitrile with chlorosulfonyl isocyanate to use this reaction to synthesize new hydantoin with a chlorosulfonyl group. Organic synthesis, NMR spectroscopy on 1H, 13C and 19F nuclei, 2D NMR spectroscopy (COSY, NOESY, HMQC, HMBC), IR spectroscopy; mass spectrometry (MS), elemental analysis, X-ray diffraction analysis, high performance liquid chromatography (HPLC), biological studies. Development of simple preparative methods for obtaining new iminohydantoin derivatives. New approaches to the construction of functionalized iminohydantoin derivatives have been developed. For the first time, a comparative analysis of synthesis methods and subsequent directions of heterocyclization of N- (2,2-dichloro-1-cyanoethenyl) urea with different substituents in the N 'position was performed. It was shown for the first time that the direction of heterocyclization of 1- (2,2-dichloro-1-cyanovinyl) -3 (di) methylureas depends on the nature of the amine: both 2,5 diamino-4-cyanooxazole (under the action of an aliphatic secondary amine) and 4.5 di (benzylamino) -1-methyl-1H-imidazol-2 (5H) -one (under excess benzylamines). Synthetic sequence developed to obtain cyclic secondary amines with trifluoromethyldiazirine substituent in multigram quantities. Scope - bioorganic chemistry.