Adamantane Derivatives Containing Thiazole Moiety: Synthesis, Antiviral and Antibacterial Activity

Abstract

Herein, we report design and synthesis of series of adamantane derivatives containing modified peptides with thiazol moiety. New compounds were synthesized in solution using TBTU (2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate) as coupling agent. All derivatives were obtained with good yields. The antiviral activity of newly synthesized compounds against influenza virus H1N1 is studied. Cytotoxicity assay for determination of CC50 were done and IC50 values were calculated. The rimantadine analogue with thiazole ring Gly-Thz-rimantadine showed good activity against influenza virus A/Hongkong/68 with IC50 = 0.11 μg/mL and CC50 = 50 μg/mL. In addition, antimicrobial and antifungal activity against model strains of gram positive (Bacillus cereus), gram negative (Escherichia coli) microorganisms and fungi strain Yarrowia lipolytica 3344 were investigated. The compounds Gly-Thz-rimantadine with good antiviral activity also showed very good antifungal activity in two different concentrations.