Abstract
A number of acylthioureas, 2-((4-methylphenoxy)methyl)-N-(aryl-carbamothioyl)benzamides (aryl = 3,5-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichloro-phenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2-bromophenyl, 2,4-dibromophenyl, 2,5-dibromophenyl, 2-iodophenyl, 3-fluorophenyl, 2,3,4-trifluorophenyl, 2,4,5-trifluoro-phenyl, 2,4,6-trifluorophenyl) have been synthesized, characterized by elemental analysis, IR and NMR spectroscopy and tested for their interaction with bacterial cells in free and adherent state. The anti-pathogenic activity was correlated with the presence of one iodine, bromide or fluorine, and two or three chloride atoms on the N-phenyl substituent of the thiourea moiety, being significant especially on Pseudomonas aeruginosa and Staphylococcus aureus strains, known for their ability to grow in biofilms. Our results demonstrate the potential of these derivatives for further development of novel anti-microbial agents with antibiofilm properties.
Highlights
IntroductionAs a result of the rapid development of resistance to the existing portfolio of antimicrobial drugs, there is an increasing need to design new antibacterial and antifungal agents with better activity profiles and lower toxicity
Nowadays antibiotic resistance has become a serious public health problem
Some pyridazine derivatives carrying thiourea moieties exhibit potent inhibitory activity against Staphylococcus aureus, Escherichia coli, Candida albicans and C. parapsilosis [2]. 1-Aroyl-3-arylthioureas showed moderate to potent activity against different bacterial strains, especially against E. coli strains resistant to standard drugs [3]
Summary
As a result of the rapid development of resistance to the existing portfolio of antimicrobial drugs, there is an increasing need to design new antibacterial and antifungal agents with better activity profiles and lower toxicity. The 1-(isomeric fluorobenzoyl)-3-(isomeric fluorophenyl)thioureas were proven to exhibit better antifungal than antibacterial activity, probably due to the inclusion of fluorine that may increase the lipophilicity and enhance the rate of cell penetration and transport of the drug to an active site. Taking into account the improvement of the antimicrobial activity by the inclusion of fluorine in the organic molecule of thioureas [7], we synthesized, characterized and studied the antimicrobial activity of the new 2-((4-methylphenoxy)methyl)-N-(arylcarbamothioyl)benzamides, substituted with phenyl groups carrying one, two or three atoms of F, Cl, Br and I
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