6α-HYDROXYPENICILLANIC ACID-S(S)-OXIDE AND ANALOGUES: SYNTHESIS AND ANTIMICROBIAL ACTIVITY

JOHN L. ROBERTS; PAT F. BEVILACQUA; DENNIS D. KEITH; BEVERLY A. PAWSON; DAVID L. PRUESS; PAMELA L. ROSSMAN

doi:10.7164/antibiotics.45.363

JOHN L. ROBERTS, PAT F. BEVILACQUA, DENNIS D. KEITH, BEVERLY A. PAWSON, DAVID L. PRUESS, PAMELA L. ROSSMAN

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JOURNAL FREE ACCESS

1992 Volume 45 Issue 3 Pages 363-373

DOI https://doi.org/10.7164/antibiotics.45.363

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Abstract

The synthesis and in vitro antibacterial activity of a series of 6-oxygenated penicillanic acid sulfoxides is described. 6α-Hydroxypenicillanic acid-S(S)-oxide (1a) exhibits weak Gram-negative antibacterial activity and appears to be similar to amdihocillin (5) in its mode of action. 6α-Hydroxypenicillanic acid-S(R)-oxide (4a) has a broader spectrum of activity, but again is rather weak. The corresponding 6β-hydroxy series is essentially devoid of activity.

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