| 2-Oxazolidone | |
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1,3-Oxazolidin-2-one |
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Other names
2-Oxazolidone |
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| Identifiers | |
| CAS number | 497-25-6 |
| PubChem | 73949 |
| ChemSpider | 66579 |
| KEGG | C06695 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C3H5NO2 |
| Molar mass | 87.077 g/mol |
| Appearance | Solid |
| Melting point |
86–89 °C |
| Boiling point |
220 °C at 48 torr |
| Related compounds | |
| Related compounds | Oxazolidine |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
2-Oxazolidone is a heterocyclic organic compound containing both nitrogen and oxygen in a 5-membered ring.
Contents |
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 mainly used as antibiotics. The antibacterial effect of oxazolidinones is by working as protein synthesis inhibitors, targeting an early step involving the binding of N-formylmethionyl-tRNA to the ribosome.[1] 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. These antibiotics are considered as a choice of last resort where every other antibiotic therapy has failed.
Examples of antibiotic oxazolidinones include:
An oxazolidinone derivative used for other purposes is rivaroxaban, which is approvedby the FDA for venous thromboembolism prophylaxis.
The first ever used oxazolidinone was Cycloserine (4-amino-1,2-oxazolidin-3-one), a second line drug against Tuberculosis since 1956.[3] Developed during the nineties when several bacterial strains were becoming resistant against such antibiotics as vancomycin. Linezolid (Zyvox) is the first approved agent in the class.
The first commercially available 1,3-oxazolidinone antibiotic was Linezolid, discovered and developed by Pharmacia & Upjohn.
In 2002 AstraZeneca introduced posizolid (AZD2563).
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