Synthesis and characterization of halogenated bis(acylthiourea) derivatives and their antibacterial activities

Abstract

<p></p> <p>A total of 12 bis(acylthiourea) derivatives with different pharmacophores have been synthesized <i>via</i> nucleophilic substitution reaction of benzene-1,4-dicarbonyl isothiocyanate intermediate with aromatic amine bearing halogens at the <i>ortho, meta</i> and <i>para</i> positions. The structures of the synthesized compounds were confirmed by CHN elemental analysis, FT-IR, ¹H NMR and ¹³C NMR spectroscopies. Antibacterial studies of the compounds <i>via</i> the Kirby Bauer disc diffusion method against <i>Escherichia coli</i> (<i>E. coli</i>) ATCC 25922 and <i>Staphylococcus aureus</i> (<i>S. aureus</i>) S48/81 demonstrated that bis(acylthiourea) <i>N¹,N⁴</i>-bis[(2-chlorophenyl)carbamothioyl]terephthalamide <b>(4)</b> and <i>N¹,N⁴</i>-bis[(2-bromophenyl)carbamothioyl]terephthalamide <b>(7)</b> bearing Cl and Br at the <i>ortho</i> position exhibited excellent activities against both bacteria strains compared to ampicillin standard.</p