Abstract
•Thiazole-linked-thiadiazoles and dithiazoles were prepared from the reaction of thiazolethiosemicarbazone derivatives with α-haloketones.•All structures of products were assured based on their spectral (IR, NMR and Mass) data.•All synthesized derivatives were examined for their antibacterial activity and three derivatives 7d, 14c and 14d showed potent activity.•Compounds 7d, 14c, and 14d displayed potential anti-biofilm activity (14d > 7d > 14c) against the three tested bacterial strains with MSSA and MRSA being more sensitive than VRSA.•Docking result indicated well-fitting and proper orientation of the dithiazole derivatives 14c and 14d into MRSA protein (PDB ID 1MWT).
In the pharmaceutical industry, both thiazole-linked-thiadiazoles and dithiazoles are known for their numerous biological activities in the treatment of many diseases. Thiazole-linked-thiadiazole and dithiazole derivatives were synthesized in this context by reacting thiazole thiosemicarbazone derivatives with hydrazonoyl chlorides, phenacyl bromides, or α‑chloro-acetyl acetone. All proposed product structures were validated using spectral (IR, NMR, and Mass) data. The antibacterial activity of all synthesized thiazole-linked-thiadiazoles and dithiazole derivatives was tested against Methicillin-sensitive Staphylococcus aureus (MSSA) ATCC 29,213, Methicillin-resistant Staphylococcus aureus (MRSA) ATCC 700,788, and vancomycin-resistant Staphylococcus aureus (VRSA) RCMB 28,354. Three derivatives, 7d, 14c, and 14d, demonstrated significant activity. Furthermore, compounds 7d, 14c, and 14d demonstrated potential anti-biofilm activity against the three tested bacterial strains (14d > 7d > 14c), with MSSA and MRSA being more sensitive than VRSA. Further to that, docking results indicated that the dithiazole derivatives 14c and 14d were well-fitting and properly oriented into MRSA protein (PDB ID 1MWT), with docking scores of -6.077 and -6.0886 Kcal/mol.
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