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Preparation and structure-activity relationships of some 6.ALPHA.-substituted penicillins.

1985; Springer Nature; Volume: 38; Issue: 6 Linguagem: Inglês

10.7164/antibiotics.38.721

1881-1469

George Burton, MICHAEL J. BASKER, P. H. BENTLEY, DESMOND J. BEST, Ronald Dixon, Frank P. Harrington, Robert F. Kenyon, Andrew G. Lashford, Andrew W. Taylor,

Synthesis and biological activity

The influence on the antibacterial activity of introducing a 6α-methoxy group into carbenicillin, and various 6α-substituents into sulbenicillin and piperacillin was examined. Further variations of the side chain aryl group were examined in the 6α-methoxy substituted series. This led to the identification of disodium 6β-(D, L-2-carboxy-2-thien-3-ylacetamido)-6α-methoxypenicillanate (5b) as a β-lactamase stable derivative with useful activity against Enterobacteriaceae, and disodium 6β-[D-2-(4-aminophenyl)-2-sulfoacetamido]-6α-methoxypenicillanate (6e) with slightly lower activity against the Enterobacteriaceae but more active against Pseudontonas aeruginosa.