Oxazolidinones are members of a group of substances saturated heterocyclic compounds bearing a five-membered ring in both a nitrogen and an oxygen atom and contain a carbonyl group. This results in either a cyclic ester ( a lactone ), cyclic amide ( lactam ), a ketone or a carbamate ( urethane ). The parent compounds of the group are the 1,3- oxazolidine and 1,2- oxazolidine ( isoxazolidine ), from which we deduce each 3 oxazolidinones.
In preparative chemistry of 1,3- oxazolidine -2-ones have long been used as auxiliaries. Some oxazolidinones are among a group of antibiotics. The first commercially available drug was cycloserine (4- amino-1 ,2- oxazolidin- 3-one) as a drug against tuberculosis in 1956. More oxazolidinones are about linezolid and eperezolid.
In preparative chemistry of 1,3- oxazolidine -2-ones serve as auxiliaries. The substance to be converted before the actual reaction with an Evans auxiliary is substituted. The voluminous auxiliary directs the reaction so that a stereoselective reaction product is preferably formed:
After the reaction has the Evans auxiliary ( here with lithium hydroxide and hydrogen peroxide) be split off again.
The medically active oxazolidinones are among the antibacterial drugs and are known protein synthesis inhibitor (as well as tetracyclines, aminoglycosides, lincosamides, and macrolides ). Oxazolidinones inhibit the onset of synthesis of a peptide strand, where self-assemble ribosome, messenger or messenger RNA and start- tRNA -AS complex. They work mostly bacteriostatic to Gram-positive bacteria; Cycloserine inhibits Gram- negative bacteria as well as Mycobacterium tuberculosis.
As a side effect of bone marrow suppression has been described, blood counts should be monitored. In Germany cycloserine itself is not used because of severe neurotoxic side effects as a drug for drug production, but in the form of the condensation product with terephthaldialdehyde terizidone, but which also looks even more neurotoxic and is therefore used only as an anti-tuberculosis drug 2nd choice.