To study and evaluate the anticholinesterase properties of the 2(5H)-furanones synthesized by us and their dicyano, imino, and thiocarbamide derivatives in relation to human erythrocyte acetylcholinesterase (AChE) and human plasma butyrylcholinesterase (BuChE), as well as their antiradical properties.The antiradical properties of the compounds were evaluated using the stable free radical 2,2'-diphenyl-1-picrylhydrazyl (DPPH•).It was found that of the tested compounds, methyl 3-{3-[5,5-disubstituted-4-methyl-3-phenylfuran-2(5H)-ylidene]-1-phenylthioureido}propanoates exhibits the highest selective activity against BuChE. The relationship between chemical structure and biological activity was analyzed. It was found that the introduction of a thiocarbamide group containing a phenyldimethylene carboxymethylate structural unit into position 2 of the 2(5H)-furan ring sharply increases the selective antibutyrylcholinesterase activity. It was also found that compounds containing a dicyanomethylene group at position 2 exhibits the highest and equal (89.1%, 89.1%) antiradical activity, exceeding the activity of gallic acid (88.8%) and approaching the effectiveness of vitamin C (93.5%), while slightly lower activity exhibits lactones containing acetyl (65.95% and 77.46%) and nitrile (49.7% and 74.1%) functional groups in position 3. The introduction of phenyl or p-methoxyphenyl substituents in position 3, on the contrary, leads to a significant decrease in activity.The data obtained confirm the relevance of functionally substituted 2(5H)-furanones as promising compounds potentially possessing anticholinesterase and antiradical activities.