2-Oxazolidone

2-Oxazolidone
IUPAC name 1,3-Oxazolidin-2-one
Other names 2-Oxazolidone 2-Oxazolidinone
Identifiers
CAS number	497-25-6 Y
PubChem	73949
ChemSpider	66579 Y
KEGG	C06695 Y
Jmol-3D images	Image 1
SMILES O=C1OCCN1
InChI InChI=1S/C3H5NO2/c5-3-4-1-2-6-3/h1-2H2,(H,4,5) Y Key: IZXIZTKNFFYFOF-UHFFFAOYSA-N Y InChI=1/C3H5NO2/c5-3-4-1-2-6-3/h1-2H2,(H,4,5) Key: IZXIZTKNFFYFOF-UHFFFAOYAE
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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2-Oxazolidone is a heterocyclic organic compound containing both nitrogen and oxygen in a 5-membered ring.

Oxazolidinones

Evans auxiliaries

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.

Pharmaceuticals

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:

• Linezolid (Zyvox), which is available for intravenous administration and also has the advantage of having excellent oral bioavailability.
• Posizolid, which appears to have excellent, targeted bactericidal activity against all common gram-positive bacteria, regardless of resistance to other classes of antibiotics.

Chemical structure of Torezolid

• Torezolid is in phase-II clinical trials
• Radezolid (RX-1741) has completed some phase-II clinical trials.^[2]
• Cycloserine is a second line drug against tuberculosis

An oxazolidinone derivative used for other purposes is rivaroxaban, which is approvedby the FDA for venous thromboembolism prophylaxis.

History

Chemical structure of Cycloserine

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.

Chemical structure of Linezolid

The first commercially available 1,3-oxazolidinone antibiotic was Linezolid, discovered and developed by Pharmacia & Upjohn.

Chemical structure of posizolid/AZD2563

In 2002 AstraZeneca introduced posizolid (AZD2563).

References

1. ^ Shinabarger, D. (1999). "Mechanism of action of the oxazolidinone antibacterial agents". Expert Opinion on Investigational Drugs 8 (8): 1195–1202. doi:10.1517/13543784.8.8.1195. PMID 15992144.  edit
2. ^ "Rx 1741". Rib-X Pharmaceuticals. 2009. http://www.rib-x.com/pipeline/rx_1741. Retrieved 2009-05-17. 
3. ^ A. W. Frahm, H. H. J. Hager, F. v. Bruchhausen, M. Albinus, H. Hager: Hagers Handbuch der pharmazeutischen Praxis: Folgeband 4: Stoffe A-K., Birkhäuser, 1999, ISBN 978-3-540-52688-9

External links

• Synthesis of Oxazolidinones - Recent Literature