This study develops a new method of synthesizing podands containing thioether fragments 1.10-bis(2-formylphenyl)-1.10-dithia-4.7-dioxadecane and 1.10-bis(2-acetophenyl)- 1.10-dithia-4.7-dioxadecane. The synthesized podands’ transformations were studied in acidic condition to obtain products of the croton condensation reaction having arylenone fragment. All the synthesized compounds’ bioactivities were predicted by PASS online programme in which podand (9) was evaluated for its antibiotic activity. The structure of the new podand was determined by IR, 1H NMR, MS spectrums.