Abstract
Staphylococcus aureus is one of the most common causes of nosocomial infections. The purpose of this study was the synthesis and in vitro evaluation of antimicrobial activity of 10 new 3-oxazolidin-2-one analogues on 12 methicillin resistant S. aureus (MRSA) clinical isolates. S. aureus confirmation was achieved via catalase and coagulase test. Molecular characterization of MRSA was performed by amplification of the mecA gene. Antimicrobial susceptibility was evaluated via the Kirby-Bauer disc diffusion susceptibility test protocol, using commonly applied antibiotics and the oxazolidinone analogues. Only (R)-5-((S)-1-dibenzylaminoethyl)-1,3-oxazolidin-2-one (7a) exhibited antibacterial activity at 6.6 μg. These results, allow us to infer that molecules such as 7a can be potentially used to treat infections caused by MRSA strains.
Highlights
Staphylococcus aureus is one of the most common causes of nosocomial infections, which can occur via the direct contamination of an open wound, such as postsurgical wound infection diseases.Since the emergence of S. aureus isolates with resistance to methicillin [1], it has become a well-known etiological agent for a wide variety of infections
The 1,3-oxazolidin-2-one analogues 6a–e and 7a–e were synthesized via initial reduction of α-aminoaldehydes 1a–e
Treatment of these analogues with lithium aluminum hydride (LiAlH4) in anhydrous diethyl ether (Et2O) at 0 °C allowed for the formation of the corresponding chiral amino alcohols 4 and 5, which were treated with bis-(trichloromethyl) carbonate (BTC) to produce the desired 5-substituted-1,3oxazolidin-2-ones in 47% to 99% yield [9]
Summary
Staphylococcus aureus is one of the most common causes of nosocomial infections, which can occur via the direct contamination of an open wound, such as postsurgical wound infection diseases. Methicillin resistance is mediated by the expression of the mecA gene, which encodes for the modified penicillin-binding protein (PBP2a or PBP2'), which has low affinity for β-lactam antibiotics and facilitates cell-wall synthesis in the presence of methicillin and other β-lactams. This gene is contained on a genetic island called the Staphylococcal chromosomal cassette mec (SCCmec). Dibenzylamino group attached to the 1,3-oxazolidinone ring through a one carbon bridge and have an asymmetric center at the C5 position of the 1,3-oxazolidinone as in the compounds previously reported These similitudes encourage us to evaluate the antimicrobial activity of the new chiral 1,3-oxazolidin-2-ones
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