2-Oxazolidone
IUPAC name	1,3-Oxazolidin-2-one
Other names	2-Oxazolidone 2-Oxazolidinone
Identifiers
CAS number	497-25-6 Y
PubChem	73949
SMILES	O=C1OCCN1
InChI	1/C3H5NO2/c5-3-4-1-2-6-3/h1-2H2,(H,4,5)
InChI key	IZXIZTKNFFYFOF-UHFFFAOYAE
ChemSpider ID	66579
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 (what is this?)  (verify) 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.

Contents 1 Oxazolidinones 1.1 Evans auxiliaries 1.2 Pharmaceuticals 2 References 3 External links

[edit] Oxazolidinones

[edit] 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.

[edit] Pharmaceuticals

Oxazolidinones are used as antibiotics. The first ever used oxazolidinone was Cycloserine (4-amino-1,2-oxazolidin-3-one), a second line drug against Tuberculosis since 1956.^[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. 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 1,3-oxazolidinone antibiotic was Linezolid. In 2002 AstraZeneca introduced posizolid (AZD2563). Results indicate that posizolid has excellent, targeted activity against all common gram-positive bacteria, regardless of resistance to other classes of antibiotics.

Another: Torezolid in in phase-II clinical trials.

The anticoagulant rivaroxaban, an oxazolidinone derivative, is undergoing trials.

[edit] References

1. ^ 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 9783540526889

[edit] External links

• Synthesis of Oxazolidinones - Recent Literature

v • d • e Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ) 30S Aminoglycosides (initiation inhibitors) -mycin (Streptomyces) Streptomycin Neomycin (Framycetin, Paromomycin, Ribostamycin) Kanamycin (Amikacin, Arbekacin, Bekanamycin, Dibekacin, Tobramycin) Spectinomycin# · Hygromycin B Paromomycin -micin (Micromonospora) Gentamicin# (Netilmicin, Sisomicin, Isepamicin) Verdamicin Astromicin Tetracycline antibiotics (tRNA binding) Tetracyclines Doxycycline#  •Chlortetracycline • Clomocycline • Demeclocycline • Lymecycline • Meclocycline • Metacycline • Minocycline • Oxytetracycline • Penimepicycline • Rolitetracycline • Tetracycline Glycylcyclines Tigecycline 50S Oxazolidinone (initiation inhibitors) Linezolid • Torezolid Peptidyl transferase Amphenicols Chloramphenicol#  · Azidamfenicol · Thiamphenicol · Florfenicol Pleuromutilins Retapamulin  · Tiamulin  · Valnemulin MLS (transpeptidation/translocation) Macrolides Erythromycin#  · Azithromycin#  · Spiramycin · Midecamycin · Oleandomycin · Roxithromycin · Josamycin · Troleandomycin · Clarithromycin · Miocamycin · Rokitamycin · Dirithromycin · Flurithromycin · Ketolide (Telithromycin, Cethromycin) Lincosamides Clindamycin#  · Lincomycin Streptogramins Pristinamycin  · Quinupristin/dalfopristin  · Virginiamycin EF-G Steroid antibacterials Fusidic acid #WHO-EM. ‡Withdrawn from market. CLINICAL TRIALS: †Phase III. §Never to phase III