Antimicrobial Activity of Some New Thioureides Derived from 2-(4-Chlorophenoxymethyl)benzoic Acid

Abstract

We report here the characterisation of eight newly synthesized thioureides of 2-(4-chlorophenoxymethyl)-benzoic acid and the evaluation of the in vitro antimicrobial activity of the new compounds against Gram-positive [Listeria monocytogenes, Staphylococcus aureus, Bacillus subtilis], Gram-negative [Psedomonas aeruginosa, Escherichia coli, Salmonella enteritidis], as well as Candida spp., using both reference and clinical multidrug resistant strains to establish the minimal inhibitory concentration (MIC) values. Our results showed that the tested compounds exhibited specific antimicrobial activities, both concerning the spectrum of antimicrobial activity and the corresponding MIC values, which ranged widely between 1024 and 32 μg/mL, depending on the nature and position of the substituents on the benzene ring. The most active compounds were N-[2-(4-chlorophenoxymethyl)-benzoyl]-N'-(2,6-dichlorophenyl)-thiourea (5g) and N-[2-(4-chlorophenoxymethyl)-benzoyl]-N'-(4-bromophenyl)-thiourea (5h), which showed a broad spectrum of antimicrobial activity against enterobacterial strains (E. coli and S. enteritidis), P. aeruginosa, S. aureus and Candida spp. All the tested compounds except 5f were highly active against S. aureus (MIC=32 μg/mL), suggesting their possible use in the treatment of MRSA infections. Four of compounds also exhibited antifungal activity (MIC =256-32 μg/mL) against C. albicans, but L. monocytogenes as well as B. subtilis were resistant to all tested compounds. Our studies thus demonstrated that among other biological activities, the thioureides of 2-(4-chlorophenoxymethyl)-benzoic acid also exhibit selective and effective antimicrobial properties that could lead to the selection and use of these compounds as efficient antimicrobial agents, especially for the treatment of multidrug resistant infections.

Synthesis and antimicrobial screening of N-(1-methyl-1H-pyrazole-4-carbonyl)-thiourea derivatives

“…Giving attention to the possible synergetic antimicrobial effects of both thiourea and pyrayole moieties presence in an organic compound and following the promising model of various phenoxymethylbenzoic acids thioureides (Limban et al, 2000(Limban et al, , 2004(Limban et al, , 2008a we synthesized a series of N-(1-methyl-1H-pyrazole-4-carbonyl)-thiourea derivatives and tested their antimicrobial potential.…”

Synthesis and microbiological activity of thiourea derivatives of 4-azatricyclo[5.2.2.02,6]undec-8-ene-3,5-dione

“…Thiourea derivatives are associated with a broad spectrum of biological activities including antibacterial, antifungal, tuberculostatic, antitumor, anticonvulsant and antiviral properties (Limbau et al, 2008;Venkatachalan et al, 2004;Aramakada et al, 2007;Bloom et al, 2004;Seth et al, 2004;Lee et al, 2003;Kaymakciglu et al, 2005;Esteves-Souza et al, 2006).…”

Synthesis and characterization of some novel bis‐thiazoles

“…Like thiazoles, bis‐thiazoles are also known for their remarkable biological activities where anticancerous, antibiotic, antimicrobial, antifungal, antibacterial, and anti‐inflammatory activities have been reported …”