A variety of new compounds containing two or three biologically active nuclei of imidazolidine-2,4-dione and thiazolidine-2,4-dione (TZD) via optimization two and three directional 3 and 4MCRs Knoevenagel condensation (method A) and two and three directional 5 and 7 MCRs Bucherer-Bergs (method B). The structure of these derivatives was confirmed by FT-IR, 1HNMR, 13CNMR, and Elemental analysis. To evaluate the anticonvulsant activity of these derivatives, all the compounds were subjected to molecular docking studies for Anticonvulsant Drug Binding (ADB) to the Voltage-Gated Sodium Channel Inner Pore (VGCIP). The in silico molecular docking study results showed that molecules 5c, 9, 7, and 10 among the synthesized compounds have the lowest docking score which shows the highest combined desire for the channel and have a good affinity toward the active pocket, thus, they may be considered good anticonvulsant agents. Also, to evaluate the antibacterial properties of these derivatives, they underwent molecular docking studies with four bacterial proteins. Gram-positive bacteria such as B. anthracis (PDB ID: 3TYE) and S. aureus (PDB ID: 3ACX) and gram-negative bacteria E. coli (PDB ID: 1AB4) and P. aeruginosa (PDB ID: 5U39). The most significant overall score has been obtained for S. aureus (PDB ID: 3ACX) bacteria. A combination of 10 displays strong antibacterial activity against two gram-positive bacterial and compounds 4a and 7 with gram-negative proteins bacterial. The highest binding affinity is related to compound 7 for gram-negative P. aeruginosa (PDB ID: 5U39) bacterial proteins. The antibacterial properties of these derivatives were as well experimentally investigated.