Oxadiazole and thiadiazole are of interest building blocks used in drug design. Considering importance of mentioned scaffolds some of the thiadiazole-oxadiazolederivatives were synthesized by three steps in this study.Firstly, thiol functions of 2-amino-5-mercapto-1, 3, 4-thiadiazole was alkylated by benzyl chloride derivatives to give compounds (1a-c). The reaction of chloroacethylchloride with amine group of compounds (1a–c) terminates to amide derivatives(2a-c). Definitive products were produced by treatment of corresponding amide derivatives with 5-(4-chlorophenyl)-1, 3, 4-oxadiazole-2-thiol.Synthesized compounds were evaluated by MTT assay against two cell lines. The final molecules were docked in the active sites of the epidermal growth factor receptor tyrosine kinase to assay the possible interactions.Final products showed range of cytotoxic activity of moderate to good against tested cell lines. Compound (3a) demonstrated a higher cytotoxic activity against MCF-7 (IC50: 26 µM) and Lncap (IC50: 37 µM) cell lines in comparison with other compounds. The highest docking score was -10.55kcal/mol for compound3a.