Premium
Synthesis and Antibacterial Activity of 4‐Aryl‐2‐(1‐substituted ethylidene)thiazoles
Author(s) -
Hassan Alaa A.,
Ibrahim Yusria R.,
ElSheref Essmat M.,
AbdelAziz Mohamed,
Bräse Stefan,
Nieger Martin
Publication year - 2013
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201300099
Subject(s) - antibacterial activity , aryl , ciprofloxacin , chemistry , bacteria , antibacterial agent , staphylococcus aureus , stereochemistry , penicillin , organic chemistry , antibiotics , biology , biochemistry , alkyl , genetics
( 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.