Synthesis and antimicrobial properties of 4-acylaminobenzenethiosulfoacid S-esters

Abstract

A series of esters of 4-acetyl, 4-trifluoroacetyl- and 4-(3-chloropropionyl)aminobenzenethiosulfoacids (twenty-four compounds) were synthesized and characterized by elemental analysis, ¹H NMR and IR spectroscopy. The antibacterial activity of the novel candidates has been screened using the agar diffusion or serial dilution methods against representative Gram-positive (<i>Staphylococcus aureus</i>, <i>Bacillus subtilis</i>, <i>Bacillus mesentericus</i>, <i>Mycobacterium</i> sp., <i>Mycobacterium luteum</i>), Gram-negative (<i>Aeromonas</i> sp., <i>Burkholderia cepacia</i>, <i>Alcaligenes faecalis</i>, <i>Pseudomonas aeruginosa</i>, <i>Escherichia coli</i>, <i>Proteus vulgaris</i>) bacteria and fungi (<i>Candida albicans</i>, <i>Candida tenuis</i>, <i>Candida glabrata</i>, <i>Verticillium dahliae</i>, <i>Trichophyton gypseum</i>, <i>Aspergillus niger</i>, <i>Aspergillus fumigatus</i>, <i>Penicillium chrysogenum</i>). Particular potency has been discovered against all tested pathogenic bacteria and fungi by compounds <b>1l</b> and <b>3l</b> at nanomolar concentrations. Some appropriate effect of thiosulfoesters structure upon their antimicrobial activity was determined.