2-Oxazolidone

Oxazolidinones are a class of compounds containing 2-oxazolidone in the structure. In chemistry, they are useful as Evans auxiliaries, which are used for chiral synthesis. Usually, the acid chloride substrate reacts with the oxazolidinone to form an imide. Substituents at the 4 and 5 position of the oxazolidinone direct any aldol reaction to the alpha position of the carbonyl of the substrate.

Oxazolidinones are used as antibiotics. Some of the most important oxazolidinones are the last generation of antibiotics used against gram-positive pathogens, including superbugs such as Methicillin-resistant Staphylococcus aureus. Developed during the nineties when several bacterial strains were becoming resistant against such antibiotics as vancomycin. These antibiotics are considered as a choice of last resort where every other antibiotic therapy has failed. Linezolid (Zyvox), the only currently available agent in this class, is available for intravenous administration and also has the advantage of having excellent oral bioavailability.

The first commercially available oxazolidinone antibiotic was Linezolid. In 2002 AstraZeneca introduced the AZD2563 antibiotic. Results indicate that AZD2563 has excellent, targeted activity against all common gram-positive bacteria, regardless of resistance to other classes of antibiotics. The anticoagulant rivaroxaban, an oxazolidinone derivative, is undergoing trials.

• Synthesis of Oxazolidinones – Recent Literature

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