Adamantane-Isothiourea Hybrid Derivatives: Synthesis, Characterization, In Vitro Antimicrobial, and In Vivo Hypoglycemic Activities

A new series of adamantane-isothiourea hybrid derivatives, namely 4-arylmethyl ( )- '-(adamantan-1-yl)-morpholine-4-carbothioimidates - and 4-arylmethyl ( )- '-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioimidates - were prepared via the reaction of -(adamantan-1-yl)morpholine-4-carbothioamide and -(adamantan-1-yl)-4-phenylpiperazine-1-carbothioamide with benzyl or substituted benzyl bromides, in acetone, in the presence of anhydrous potassium carbonate. The structures of the synthesized compounds were confirmed by ¹H-NMR, C-NMR, electrospray ionization mass spectral (ESI-MS) data, and X-ray crystallographic data. The in vitro antimicrobial activity of the new compounds was determined against certain standard strains of pathogenic bacteria and the yeast-like pathogenic fungus . Compounds , and displayed potent broad-spectrum antibacterial activity, while compounds , , , and were active against the tested Gram-positive bacteria. The in vivo oral hypoglycemic activity of the new compounds was carried on streptozotocin (STZ)-induced diabetic rats. Compounds , , and produced potent dose-independent reduction of serum glucose levels, compared to the potent hypoglycemic drug gliclazide.