Synthesis of thiourea and sugar derivatives of some chiral aromatic compounds and investigations of their biological activities

In this study, L-isoleucine, D-phenylglycine, D-phenylalanine and L-valine were used as starting amino acids. First of all, N-Boc-amino acids derivatives were synthesized. Amide derivatives were obtained by the reaction of these amino acids with o-phenylenediamine. N-Boc-chiral derivative of benzimidazoles were synthesized by inserting N-Boc amide derivatives into cyclization reaciton in an acidic environment. The synthesized N-Boc-chiral derivative of benzimidazoles were deprotected by reducing the protective group which was connected to amine group for obtaining chiral derivative of deprotected benzimidazoles. Then acetylated isothiocyanates were synthesized from 3 different monosaccharides (D-glucose, D-galactose, D-mannose). 12 original compounds (18-29) were obtained by the reaction of synthesized amide (4, 6, 8) and benzimidazole (12, 13, 14) compounds with isothiocynates. The products were characterized by spectroscopic methods (IR, 1H-NMR, 13C-NMR) and elemental analysis. Biological activities of the newly synthesized glycosyl thiourea derivative compounds were tested.