Synthesis and Antibacterial Properties of Oxazolidinones and Oxazinanones

Abstract

Oxazolidinones are important synthetic antibacterial agents useful for the treatment of multi antibiotic resistant Gram-positive bacterial infections. Since the launch of Linezolid, the first member of the oxazolidinone antibacterial family, there have been many studies directed towards structural optimization and the development of second generation oxazolidinones. The N-aryl 5-acetamido methyl oxazolidinone is the core structure for this class of antibacterial agents and the oxazolidinone component is essential for antibacterial activities. The chiral cyclic carbamate 5-hydroxymethyloxazolidin-2-one and 6-hydroxymethyl-[1,3]oxazinan-2-one are also important building blocks for synthesizing other biologically active compounds. Because of the importance of these compounds, many methods have been developed for their facile syntheses. In the first part of this paper, the synthesis of Linezolid and its analogs, as well as the preparation of the oxazolidinone core structures, will be reviewed. Secondly, recent developments in the area of oxazolidinone antibacterial agents including structure-activity relationships will be reviewed.

Diversification of a β-lactam pharmacophore via allylic C–H amination: accelerating effect of Lewis acid co-catalyst

“…For example, oxazolidinones are the key structural unit in a new class of synthetic antibacterial agents for treatment of multi-drug resistant Gram-positive bacterial infections (e.g. Linezolid) 10. Linear allylic amines 12 and (+)- 14 were also easily deprotected using similarly mild Na/naphthalene conditions in 84% and 89% yield, respectively.…”

“…We anticipated that these allylic C—H amination reactions would provide a highly efficient means of introducing pharmacologically interesting nitrogen functionality (i.e. oxazolidinones, oxazinanones, linear amines)10 onto molecules containing sensitive β-lactam cores (Figure 1). …”

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“…The synthesis of impurities were reported in the literature [8][9][10], but the process was having low yield with several steps [11].…”

Green Catalytic Synthesis of Heterocyclic Structures Using Carbon Dioxide and Related Motifs

“…Besides linezolid, also other oxazolidinone structures have been reported to have effective antimicrobial activity including tedizolid and posizolid ( Figure 2) [27]. The former one is currently being developed and is passing through clinical trials; it is used specifically for complicated skin and skin-structure infections.…”