Synthesis and Antibacterial Activity of 4‐Aryl‐2‐(1‐substituted ethylidene)thiazoles

(E)‐4‐Aryl‐2‐[2‐(1‐substituted ethylidene)hydrazinyl]thiazoles and (Z)‐3‐substituted‐4‐aryl‐2‐[(E)‐(1‐phenylethylidene)hydrazono]‐2,3‐dihydrothiazoles were synthesized by the reaction of (substituted ethylidene)hydrazinecarbothioamides with ω‐bromoacetophenones. The characterization of this new class of compounds was performed using different spectroscopic tools. The structure of (Z)‐3‐benzyl‐4‐(4‐bromophenyl)‐2‐[(E)‐(1‐phenylethylidene)hydrazono]‐2,3‐dihydrothiazole 6e was unambiguously confirmed by single‐crystal X‐ray crystallography. Compounds 5a–e, 5i, 6e, 6g, and 6i were screened for their in vitro antibacterial activity against different strains of microorganisms; most of the tested compounds exhibited promising antibacterial activity against some organisms compared to ciprofloxacin and sulbactam penicillin. Compounds 5e, 5i, 6e, 6g, and 6i exhibited several‐fold significant antibacterial activity against the Gram‐positive bacteria Staphylococcus aureus, better than ciprofloxacin, with minimum inhibitory concentration values ranging from 0.05 to 0.4 µg/mL. The rest of the tested compounds gave significant antibacterial activities against different Gram‐negative bacterial strains.

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