Synthesis and antimicrobial activity of a {2-[2-(N,N-disubstituted thiocarbamoyl-sulfanyl)-acylamino]thiazol-4-yl}acetic acid ethyl esters

Abstract

{2-[2-(N,N-Disubstituted thiocarbamoyl-sulfanyl)acylamino]thiazol-4-yl}acetic acid ethyl esters (3 a-x) were synthesized by the reaction of potassium salts of N,N-disubstituted dithiocarbamoic acids with [2-(2-chloroalkanoyl)amino-thiazol-4-yl]acetic acid ethyl esters. The structures of the synthesized compounds were confirmed by elemental analyses, UV, IR, H-1-NMR, and El mass spectral data. The antimicrobial activities of all the compounds were investigated by microbroth dilution technique using Mueller-Hinton broth and Mueller-Hinton agar. In this study, Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, Escherichia coli ATCC 8739, Klebsiella pneumoniae ATCC 4352, Pseudomonas aeruginosa ATCC 1539, Salmonella typhi, Shigella flexneri, Proteus mirabilis ATCC 14153 and Candida albicans ATCC 10231 were used as test microorganisms. Among the tested compounds 3 a, d, e, f, h, k, w showed activity against S. epidermidis ATCC 12228 (MIC: 156 mg/L, 78 mg/L, 62.5 mg/L, 78 mg/L, 62.5 mg/L, 312 mg/L, 250 mg/L, respectively), compound 3 d also had some activity against S. aureus ATCC 6538 (MIC: 156 mg/L) and C. albicans ATCC 10231 (MIC: 156 mg/L). Compounds 31, 3 x were also evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system and BACTEC 12B medium. The preliminary results indicated that all of the tested compounds were inactive against the test organism.