title: Synthesis and elastase inhibitory activity of 6 alpha-chloro-2,2-dimethyl-3 alpha-(pivaloyloxy)methylpenam sulfone, 6 alpha-chloro-2,2-dimethyl-3-exo-methylenepenam sulfone, benzyl and methyl 6 alpha-substituted penicillanate sulfones.
abstract: The triflates and pivalates of 3 alpha-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.
authors.affiliation: Instituto de Química Orgánica de Síntesis (CONICET-UNR), Rosario, Argentina.
authors.forename: C E
authors.initials: CE
authors.lastname: Boschetti
authors.forename: O A
authors.initials: OA
authors.lastname: Mascaretti
authors.forename: J A
authors.initials: JA
authors.lastname: Cricco
authors.forename: O A
authors.initials: OA
authors.lastname: Roveri
mesh_terms: D000818:Animals; D015394:Molecular Structure; D010196:Pancreatic Elastase / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship; D013407:Sulbactam / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013450:Sulfones / Q000138:chemical synthesis* / Q000494:pharmacology; D013552:Swine
chemical_list: D013450:Sulfones; D010196:Pancreatic Elastase; D013407:Sulbactam