Synthesis and antibacterial activities of N-substituted-glycinyl 1H-1,2,3-triazolyl oxazolidinones

• We synthesized N-substituted glycinyl 1H-1,2,3-triazolyl oxazolidinones.
• Compounds demonstrated moderate to strong Gram-positive antibacterial activities.
• Compounds 6u and 6v showed excellent Gram-positive antibacterial activity.
• Compounds 6m and 6n showed remarkable antibacterial activity against Moraxella catarrhalis.
• Compounds 6m, 6n, 6u and 6v demonstrated superior antibacterial activities compared to linezolid.

A series of 1H-1,2,3-triazolyl piperazino oxazolidinone analogs with optionally varied glycinyl substitutions were synthesized and their antibacterial activity assessed against a panel of susceptible and resistant Gram-positive and selected Gram-negative bacteria including clinical isolates. The N-aroyl- and N-heteroaroyl-glycinyl (MIC: 0.06–4 μg/ml) derivatives were more potent than the N-acylglycinyl (2–8 μg/ml) derivatives against all Gram-positive bacteria tested. Nitro substitution on aryl and heteroaryl rings significantly enhanced activity against Gram-positive bacteria, as noted with the 3,5-dinitrobenzoyl (6m and 6n) and 5-nitro-2-furoyl (6u and 6v) derivatives with MIC ranges of and 0.25–0.5 and 0.06–0.5 μg/ml, respectively. These nitro analogs also showed more potent extended activity against Moraxella catarrhalis, with MICs ranges of 0.25–1 μg/ml, compared to linezolid (MIC: 8 μg/ml). Hence, the presence of the N-aroyl and/or N-heteroaroyl glycinyl structural motifs as spacer group could significantly enhance the antibacterial activities of 1H-1,2,3-triazolyl oxazolidinone class of compounds.

A series of N-substituedglycinyl-1H-1,2,3-triazolyl oxazolidinone derivatives were synthesized and evaluated for antibacterial activities against Gram-positive and Gram-negative susceptible and resistant clinical isolates.Figure optionsDownload as PowerPoint slide