Synthesis and β-lactamase inhibitory properties of 2β-[1,2,3-triazol-1-yl)methyl]-2α-methylpenam-3α-carboxylic acid 1,1-dioxide and related triazolyl derivatives

Article abstract of DOI:10.1021/jm00391a032

Benzhydryl 2β-[(1,2,3-triazol-yl)methyl]-2α-methylpenam-3α-carboxylate 1,1-dioxide was prepared by heating benzhydryl 2β-(azidomethyl)-2α-methylpenam-3α-carboxylate 1,1-dioxide with (trimethylsilyl)acetylene. The ester group was removed by hydrogenolysis to give sodium 2β-[(1,2,3-triazol-1-yl)methyl]-2α-methylpenam-3α-carboxylate 1,1-dioxide (3i, YTR-830), which was found to be a potent inhibitor of various bacterial β-lactamases. A series of related compounds was prepared in a similar way, and all of these compounds show excellent β-lactamase inhibitory properties.