Molecular docking and glucosidase inhibition studies of novel N-arylthiazole-2-amines and Ethyl 2-[aryl(thiazol-2-yl)amino]acetates

This study describes an efficient synthesis of a series of novel ethyl 2-[aryl(thiazol-2-yl)amino]acetates ( 4a – l ) from N -arylthiazole-2-amines ( 3a – l ). The reaction conditions were optimized and the best results were obtained when ethyl chloroacetate was used as alkylating agent and NaH as base in THF. α- glucosidase and β -glucosidase inhibition activities of N -arylthiazole-2-amines ( 3a – l ) and ethyl 2-[aryl(thiazol-2-yl)amino]acetates ( 4a – l ) were determined, which revealed that most of the compounds showed high percentage inhibition towards the enzymes. Among the synthesized compounds, 4e appeared to have the highest inhibition towards α-glucosidase having IC 50 value of 150.4 ± 1.9 μM which was almost two folds as compared to acarbose (336.9 ± 9.0 μM) taken as standard. Molecular docking of the compounds 3g , 3f , 4a , and 4e was also performed which showed their bonding modes to the enzyme’s active sites via amino and acetate groups, respectively.