146039-52-3Relevant academic research and scientific papers
Alkylidene oxapenem β-lactamase inhibitors revisited: Potent broad spectrum activity but new stability challenges
Miller, Matthew D.,Kale, Manoj,Reddy, Kishore,Tentarelli, Sharon,Zambrowski, Mark,Zhang, Minli,Palmer, Tiffany,Breen, John,Lahiri, Sushmita,Shirude, Pravin S.,Verheijen, Jeroen C.
, p. 915 - 920 (2014)
We present a comprehensive study of C6-alkylidene containing oxapenems. We show that this class of β-lactamase inhibitors possesses an unprecedented spectrum with activity against class A, C, and D enzymes. Surprisingly, this class of compounds displayed significant photolytic instability in addition to the known hydrolytic instability. Quantum mechanical calculations were used to develop models to predict the stability of new analogues.
First synthetic access to 6-(methylene)oxapenems: A new class of β-lactamase inhibitors
Wild,Hartwig
, p. 1099 - 1103 (2007/10/02)
The first synthetic route to racemic 6-(substituted methylene)oxapenems, an interesting new class of β-lactamase inhibitors, is described. In spite of their low hydrolytic stability, even the unprotected acids 9 and 10 can be isolated as their sodium salts. The 6-(unsubstituted methylene)oxapenem 7e, however, is unstable and decomposes under the conditions of its formation.
