Antimicrobial activity of some new thioureides derived from 2-(4-chlorophenoxymethyl)benzoic acid.
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 mug/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 (5 g) 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 mug/mL), suggesting their possible use in the treatment of MRSA infections. Four of compounds also exhibited antifungal activity (MIC =256-32 microg/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.
Limban
Carmen
C
Pharmaceutical Chemistry Department, Faculty of Farmacy, Carol Davila University of Medicine and Pharmacy, Traian Vuia 6, sect. 2, 020956, Bucharest, Romania. carmen_chifiriuc@yahoo.com
Chifiriuc
Mariana-Carmen Balotescu
MC
Missir
Alexandru-Vasile
AV
Chiriţă
Ileana Cornelia
IC
Bleotu
Coralia
C
D017304:Annexin A5 / Q000378:metabolism; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D019817:Benzoic Acid / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002733:Chlorophenols; D005434:Flow Cytometry; D005658:Fungi / Q000187:drug effects; D006367:HeLa Cells; D006801:Humans; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D013890:Thiourea / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
C529841:2-(4-chlorophenoxymethyl)benzoic acid; D017304:Annexin A5; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001565:Benzoates; D002733:Chlorophenols; D006845:Hydrocarbons, Fluorinated; D019817:Benzoic Acid; D013890:Thiourea