The synthesis and evaluation of 6-alkylidene-2ʹβ-substituted penam sulfones as β-lactamase inhibitors

Penicillin sulfones, which structurally incorporate both a 6-position alkylidene substituent and a 2ʹβ substituent, have been synthesized and evaluated as inhibitors of class C and class A serine β-lactamases. Incorporation of the 2ʹβ-substituent generally improves inhibitory activity. Substituents that improve transport across the bacterial cell membrane have also been incorporated.