In the present work, a library of fifteen 2-hydroxy benzothiazole-linked 1,3,4 -oxadiazole derivatives have been synthesized and confirmed using different analytical techniques. All of the synthesized compounds have been tested for antibacterial and in silico pharmacokinetic studies for the first time. From the ADME predictions, compound 4 showed the highest in silico absorption percentage (86.77%), while most of the compounds showed more than 70% absorption. All of the compounds comply with the Lipinski rule of 5, suggesting that the compounds possess good drug likeness properties upon administration. Furthermore, all of the compounds follow the Veber rule, indicating good bioavailability and good intestinal absorption. The antibacterial results exhibited excellent to moderate activity. Compounds 5, 9, 12, 14, 15, 16, and 17 were the most active compounds against the tested bacterial strains. Compound 14 showed comparable MIC 6.25 +/- 0.2 mu g/disc to the standard drug amoxicillin against the tested Gram-positive bacterial strains. Compounds 5, 14, 17 exhibited MIC 12.5 +/- 0.8 mu g/disc, which was comparable to the standard drug against E. faecalis. It can be concluded that the synthesized compound could be used as a lead molecule in the development of new antibacterial agents with high efficacy.