100192-61-8Relevant academic research and scientific papers
N-Acyl and N-sulfonyloxazolidine-2,4-diones are pseudo-irreversible inhibitors of serine proteases
Santana, Ana Bela,Lucas, Susana D.,Goncalves, Lidia M.,Correia, Henrique F.,Cardote, Teresa A.F.,Guedes, Rita C.,Iley, Jim,Moreira, Rui
supporting information; experimental part, p. 3993 - 3997 (2012/07/03)
The synthesis, inhibitory activity and mode of action of oxazolidine-2,4-diones against porcine pancreatic elastase, here used as a model for human neutrophil elastase, are reported. The nature of N-substitution at the oxazolidine-2,4-dione scaffold has large effect on the inhibitory potency against elastase. N-Acyl and N-sulfonyloxazolidine-2,4-diones emerged as potent pseudo-irreversible inhibitors, displaying high second-order rate constants for PPE inactivation. The title compounds were also shown to be potent inhibitors of human neutrophil elastase (HNE) and proteinase-3, and weak inhibitors of human cathepsin G. The results herein presented show that the oxazolidine-2,4-diones represent a new promising class of serine protease inhibitors.
2(3H)-oxazolones from α-hydroxy amides and keteneylidenetriphenylphosphorane via a phoshorus ylide cascade
Loeffler, Jonas,Schobert, Rainer
, p. 217 - 220 (2007/10/03)
Upon heating in xylene α-hydroxyamides 3 react with the cumulated phosphorus ylide 1 to give the substituted 2(3H)-oxazolones 8 in 40-80% yield. The reaction proceeds via an addition/cyclization/intermolecular-Wittig olefination sequence, which implies th
Electrochemical Studies on Haloamides. Part XII. Electrosynthesis of Oxazolidine-2,4-diones
Casadei, Maria Antonietta,Cesa, Stefania,Inesi, Achille
, p. 5891 - 5900 (2007/10/02)
Electrogenerated bases promote the carboxylation of NH-protic carboxamides bearing a leaving group at the position 2 to give oxazolidine-2,4-diones.The process is believed to involve acid-base reaction with the substrate, carboxylation of its conjugate base to corresponding carbamate and ring-closure following intramolecular SN2 reaction.A variety of oxazolidine-2,4-diones, including clinically used trimethadione and malidone, have been prepared in high to excellent yield, which established the scope and generality of this new ring-forming process.
