This project was designed to measure the enzyme inhibition potential of the synthesized compounds. The following compounds 3-amino-2-thioxothiazolidin-4-one (1) and 5-(4-chlorobenzylidene)-3-(methyleneamino)-2-thioxothiazolidin-4-one (2) were prepared via three-step method using cheaper reagents. The compounds were characterized by employing different spectroscopic techniques and subjected to biological evaluation. In vitro model was used for enzyme inhibition activity through spectrophotometer and suggested that compounds may be helpful in the medicinal field. Compound 2 exhibits more inhibition against BChE (67.7%) while compound 1 showed maximum inhibition of α-glucosidase (65.1%). Theoretical study i.e. docking of the prepared compounds was also related to experimental work. In-Silico ADMET study of both compounds exhibited various therapeutic properties, which depicted that they are quite similar to the drug-like candidates.