S-Aminosulfeniminopenicillins: Multimode β-Lactamase Inhibitors and Template Structures for Penicillin-Based β-Lactamase Substrates as Prodrugs

TP Smyth, ME O'Donnell, MJ O'Conno…

Index: Smyth, Timothy P.; O'Donnell, Michael E.; O'Connor, Michael J.; St Ledger, James O. Journal of Organic Chemistry, 1998 , vol. 63, # 22 p. 7600 - 7618

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Citation Number: 18

Abstract

A series of novel penicillins, bearing an S-aminosulfenimine (R'(R'') NSN) side chain at the 6- position, have been prepared by direct reaction of a penicillin ester with sulfur diimides. A set of these structures, with the thiazolidine-ring sulfur in the sulfide oxidation state, exhibited a pattern of reactivity not previously encountered in penicillin chemistry, viz., cleavage of the β-lactam ring resulted in a rapid intramolecular displacement of the S-amino moiety as R'( ...