2-Oxazolidinone

2-Oxazolidone

Names
IUPAC name 1,3-Oxazolidin-2-one
Other names 2-Oxazolidone 2-Oxazolidinone
Identifiers
CAS Number	497-25-6 Y
3D model (JSmol)	Interactive image
ChemSpider	66579 Y
ECHA InfoCard	100.007.129
KEGG	C06695 Y
PubChem CID	73949
CompTox Dashboard (EPA)	DTXSID2074326
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
SMILES O=C1OCCN1
Properties
Chemical formula	C3H5NO2
Molar mass	87.077 g/mol
Appearance	Solid
Melting point	86 to 89 °C (187 to 192 °F; 359 to 362 K)
Boiling point	220 °C (428 °F; 493 K) at 48 torr
Related compounds
Related compounds	Oxazolidine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) 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 antimicrobials. 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. (See Linezolid#Mechanism of action)

Some of the most important oxazolidinones are antibiotics.

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 tedizolid

• Tedizolid, (Sivextro) which is approved for acute skin infections
• Radezolid (RX-1741) has completed some phase-II clinical trials.
• Cycloserine is a second line drug against tuberculosis. Note that cycloserine, while technically an oxazolidone, has a different mechanism of action and substantially different properties from the aforementioned compounds.
• Contezolid (S)-5-((isoxazol-3-ylamino)methyl)-3-(2,3,5-trifluoro-4-(4-oxo-3,4-dihydropyridin-1(2H)-yl)phenyl)oxazolidin-2-one (MRX-I) has reported phase 1 data and completed phase II trials in 2015, and is starting a phase 3 trial in 2016.

An oxazolidinone derivative used for other purposes is rivaroxaban, which is approved by 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.

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 (FDA approval April 2000).

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).

See also

• Oxazolidine - the ring without the carbonyl group
• Oxazolone - the unsaturated analogues

External links

• Synthesis of Oxazolidinones - Recent Literature