Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity.
C-5-substituted triazole-oxazolidinones were synthesized using a bromide catalyzed cycloaddition between aryl isocyanates and epibromohydrin followed by a three-component Huisgen cycloaddition. The library of compounds was screened for antibacterial activity against Mycobacterium smegmatis ATCC 14468, Bacillus subtilis ATCC 6633, and Enterococcus faecalis ATCC 29212. Notably, the 3-(4-acetyl-phenyl)-5-(1H-1,2,3-triazol-1-yl)methyl)-oxazolidin-2-one (18) showed an MIC of 1 microg/mL against M. smegmatis ATCC 14468, fourfold lower than the MIC measured for isoniazid.
Demaray
Jeffrey A
JA
The University of Toledo, Department of Chemistry, 2801 W. Bancroft Street, Toledo, OH 43606, USA.
Thuener
Jason E
JE
Dawson
Matthew N
MN
Sucheck
Steven J
SJ
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001412:Bacillus subtilis / Q000187:drug effects; D013293:Enterococcus faecalis / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D020102:Mycobacterium smegmatis / Q000187:drug effects; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000494:pharmacology*; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D023303:Oxazolidinones; D014230:Triazoles