Synthesis and Antioxidant Activity of New Thiazole Analogues Possessing Urea, Thiourea, and Selenourea Functionality

A new series of urea, thiourea, and selenourea derivatives with thiazole moieties were synthesized by the nucleophilic addition reaction of (2-amino-4-(3-chlorophenyl)thiazol-5-yl)(2-chlorophenyl)methanone with various substituted isocyanates/ isothiocyanates/isoselenocynates in acetone having a catalytic amount of sodium hydroxide at room temperature with good yields. All the synthesized compounds were fully characterized by spectroscopic data and screened for their in vitro antioxidant activity using 1,1-diphenylpicrylhydrazyl (DPPH), nitric oxide (NO), and hydrogen peroxide (H2O2) radical scavenging methods. A preliminary study of the structure-activity relationship revealed that the compounds containing selenourea functionality along with halogen group have exhibited potent activity (IC(50)0.0309 mu mol/mL) compared to the standards (IC(50)0.0814 mu mol/mL). Thus the title compounds are a new class of potent antioxidant agents and worthy of further investigation.