Synthesis and elastase inhibitory activity of 6α-chloro-2,2-dimethyl-3α-(pivaloyloxy)methylpenam sulfone, 6α-chloro-2,2-dimethyl-3-exo-methylenepenam sulfone, benzyl and methyl 6α-substituted penicillanate sulfones Original Research Article

The triflates and pivalates of 3α-hydroxymethyl-6-substituted-2,2-dimethylpenam sulfones 3, 5; methyl and benzyl 6-substituted penicillanates 6–9 and 3-exo-methylene-6-substituted-2,2-dimethylpenam sulfone 4 were synthesized. These novel compounds were evaluated as elastase inhibitors using porcine pancreatic elastase. The effects that structural modifications of substituents on C-3 and C-6 in the penam nucleus have on elastase activity were examined and several similarities and distinctions were identified when compared to the reported penicillin esters and amides elastase inhibitors.