Synthesis and beta-lactamase inhibitory activity of new 6beta-cysteinesulfonamidopenicillanic acids

New 6beta-cysteinesulfonamidopenicillanic acids and their sulfoxides were synthesized by sulfonylation of 6beta-aminopenicillanic acid or its (S)-sulfoxide with (R)-N-benzyloxycarbonylcysteinesulfonyl chloride ethyl ester (2a, 1b) and (R)-N-benzyloxycarbonylcysteinesulfonyl chloride benzyl ester (2a...

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Published inBioorganic & medicinal chemistry Vol. 7; no. 12; p. 2899
Main Authors Changov, L S, Naydenova, E D, Ivanova, G I, Gergova, R T, Keuleyan, E E, Aleksiev, B V
Format Journal Article
LanguageEnglish
Published England 01.12.1999
Subjects
beta-Lactamase Inhibitors
Drug Interactions
Drug Resistance, Microbial
Drug Therapy, Combination - pharmacology
Gram-Negative Bacteria - drug effects
Gram-Positive Bacteria - drug effects
Magnetic Resonance Spectroscopy
Penicillanic Acid - analogs & derivatives
Penicillanic Acid - chemical synthesis
Penicillanic Acid - pharmacology
Structure-Activity Relationship
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Summary:New 6beta-cysteinesulfonamidopenicillanic acids and their sulfoxides were synthesized by sulfonylation of 6beta-aminopenicillanic acid or its (S)-sulfoxide with (R)-N-benzyloxycarbonylcysteinesulfonyl chloride ethyl ester (2a, 1b) and (R)-N-benzyloxycarbonylcysteinesulfonyl chloride benzyl ester (2a, 2b). The corresponding 6beta-cysteinesulfonamidopenicillanic acids sulfones 1c and 2c were prepared by oxidation of the sulfoxides 1b and 2b with potassium permanganate in aqueous medium. When combined with ampicillin some of the compounds reduced the minimal inhibitory concentrations of ampicillin against beta-lactamase producing strains.
ISSN:0968-0896
1464-3391