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Chemical Compound Review:

2-Oxazolidone 1,3-oxazolidin-2-one

Synonyms: Oxazolidone, Oxazolidinone, PubChem8624, SureCN4198, SureCN80643, ...

Ranaldi, G. et al., Goutopoulos, A. et al., Anthony, M.L. et al., Davies, S.G. et al., Seo, W.D. et al., et al.

Lautens, Han,

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High impact information on oxazolidin-2-one

Excellent divergent selectivity to five- vs. six-membered heterocycles is observed: alpha-alkylation/5-exo-tet cyclization (Z = NPh(2)) vs. gamma-alkylation/6-exo-trig cyclization (Z = 2-oxazolidone) [1].
Transport of the antibacterial agent oxazolidin-2-one and derivatives across intestinal (Caco-2) and renal (MDCK) epithelial cell lines [2].
The transepithelial passage of the orally bioavailable antibacterial agent oxazolidin-2-one (OXa) and 10 derivatives has been studied with human intestinal (Caco-2) and canine renal (MDCK) cell lines grown on polycarbonate filters [2].
3-[4-[(3-Chlorophenyl)methoxy]phenyl]-5-[(methylamino)methyl]- 2-oxazolidinone (1) is a secondary amine known to be a potent time-dependent irreversible inactivator of monoamine oxidase B (MAO-B) [3].
The successful hydrolysis of the oxazolidin-2-one group in both cis- and trans-derivatives show this to be a stereodivergent route to enantiopure alpha-hydroxy-beta-amino isopentanoic acids (2R,3S)-1 and (2S,3S)-2 [4].

Biological context of oxazolidin-2-one

The primary 1H NMR-detectable transformation during a 24 h incubation of confluent Madin Darby canine kidney (MDCK) cells with BEA, CEA, and FEA (at concentrations up to the IC50 determined by neutral red uptake) was the appearance in cell culture media of 2-oxazolidone (OX) [5].
This permeation enhancer is said to optimize the delivery of active ingredients into or through the stratum corneum: the 4-decyl oxazolidin-2-one [6].
Enantiomerically pure 2-methyl arachidonic acids were synthesized through diastereoselective methylation of the respective chiral 2-oxazolidinone enolate derivatives and CB1 and CB2 receptor affinities of the resulting chiral anandamides were evaluated using a standard receptor binding assay [7].
N-acyl derivatives of oxazinanones undergo stereoselective enolate alkylation reactions, with higher stereoselectivities observed for the enolate alkylation of (R)-N-propanoyl-4-iso-propyl-6,6-dimethyl-oxazinan-2-one than the corresponding Evans oxazolidin-2-one [8].

Associations of oxazolidin-2-one with other chemical compounds

The BEA metabolite aziridine was detected by 1H and 2H NMR spectroscopy of the urine 8 hr p.d. together with BEA itself and two novel metabolites 2-oxazolidone (OX) and 5-hydroxy-2-oxazolidone (HOX) [9].
After liquid-liquid extraction and derivatization with phosgene in an aqueous pH 10.1 buffer, the cyclic oxazolidone derivative is quantitated with a clenbuterol analogue as internal standard (NAB-760 Cl) [10].

References

Divergent selectivity in MgI(2)-mediated ring expansions of methylenecyclopropyl amides and imides. Lautens, M., Han, W. J. Am. Chem. Soc. (2002) [Pubmed]
Transport of the antibacterial agent oxazolidin-2-one and derivatives across intestinal (Caco-2) and renal (MDCK) epithelial cell lines. Ranaldi, G., Seneci, P., Guba, W., Islam, K., Sambuy, Y. Antimicrob. Agents Chemother. (1996) [Pubmed]
Transformation of heterocyclic reversible monoamine oxidase-B inactivators into irreversible inactivators by N-methylation. Ding, C.Z., Silverman, R.B. J. Med. Chem. (1993) [Pubmed]
Highly diastereoselective epimerization: stereodivergent synthesis of alpha-hydroxy-beta-amino isopentanoic acid. Seo, W.D., Curtis-Long, M.J., Ryu, Y.B., Lee, J.H., Yang, M.S., Lee, W.S., Park, K.H. J. Org. Chem. (2006) [Pubmed]
1H NMR spectroscopic studies on the reactions of haloalkylamines with bicarbonate ions: formation of N-carbamates and 2-oxazolidones in cell culture media and blood plasma. Anthony, M.L., Holmes, E., McDowell, P.C., Gray, T.J., Blackmore, M., Nicholson, J.K. Chem. Res. Toxicol. (1995) [Pubmed]
Black foam films from aqueous solutions of a mixture of phospholipids and a permeation enhancer. Tranchant, J.F., Bonté, F., Leroy, S., Nedyalkov, M., Platikanov, D., Javierre, I., Benattar, J.J. Journal of colloid and interface science. (2002) [Pubmed]
Stereochemical selectivity of methanandamides for the CB1 and CB2 cannabinoid receptors and their metabolic stability. Goutopoulos, A., Fan, P., Khanolkar, A.D., Xie, X.Q., Lin, S., Makriyannis, A. Bioorg. Med. Chem. (2001) [Pubmed]
Oxazinanones as chiral auxiliaries: synthesis and evaluation in enolate alkylations and aldol reactions. Davies, S.G., Garner, A.C., Roberts, P.M., Smith, A.D., Sweet, M.J., Thomson, J.E. Org. Biomol. Chem. (2006) [Pubmed]
1H and 2H NMR spectroscopic studies on the metabolism and biochemical effects of 2-bromoethanamine in the rat. Holmes, E., Caddick, S., Lindon, J.C., Wilson, I.D., Kryvawych, S., Nicholson, J.K. Biochem. Pharmacol. (1995) [Pubmed]
Determination of clenbuterol in cattle, sheep, and swine tissues by electron ionization gas chromatography/mass spectrometry. Wilson, R.T., Groneck, J.M., Holland, K.P., Henry, A.C. Journal of AOAC International. (1994) [Pubmed]

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