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Wikipedia - 2-Oxazolidone

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2-Oxazolidone
IUPAC name
1,3-Oxazolidin-2-one
Other names
2-Oxazolidone
2-Oxazolidinone
Identifiers
CAS number 497-25-6 YesY
PubChem 73949
ChemSpider 66579
SMILES
InChI
InChI 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
 YesY (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

[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

Chemical structure of Cycloserine

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.


Chemical structure of Linezolid

The first commercially available 1,3-oxazolidinone antibiotic was Linezolid.

Chemical structure of posizolid/AZD2563

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.

Chemical structure of Torezolid

Other antibiotics:

  • Torezolid is in phase-II clinical trials,
  • radezolid (RX-1741) has completed some phase-II clinical trials.[2]

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
  2. ^ "Rx 1741". Rib-X Pharmaceuticals. 2009. http://www.rib-x.com/pipeline/rx_1741. Retrieved 2009-05-17. 

[edit] External links

v • d • e
Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)
30S
-mycin (Streptomyces)
Tetracyclines
50S
Oxazolidinone
(initiation inhibitors)
EF-G
Steroid antibacterials
#WHO-EM. ‡Withdrawn from market. CLINICAL TRIALS: †Phase III. §Never to phase III

M: BAC

drug(J1p, w, n, m, vacc)
Retrieved from "http://en.wikipedia.org/wiki/2-Oxazolidone"

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "2-Oxazolidone".

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