Synthesis of cephems bearing olefinic sulfoxide side chains as potential β-lactamase inhibitors

Bioorganic & Medicinal Chemistry Letters
1996.0

Abstract

Several cephems bearing vinyl sulfoxide and suffone moieties at C-3 were prepared by the Stille coupling of a 3-trifloxy cephem with stannanes. The sulfoxides were designed to be suicide lactamase inhibitors. None of the cephems described in this study functioned as an enzyme inhibitor, but two derivatives displayed interesting biological activity against Methycillin - resistant S. Aureus.

Knowledge Graph

Similar Paper

Synthesis of cephems bearing olefinic sulfoxide side chains as potential β-lactamase inhibitors
Bioorganic & Medicinal Chemistry Letters 1996.0
Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety
Bioorganic & Medicinal Chemistry 2008.0
Synthetic studies on β-lactam antibiotics. Part 10. Synthesis of 7β-[2-carboxy-2-(4-hydroxyphenyl)acetamido]-7.alpha.-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-1-oxa-1-dethia-3-cephem-4-carboxylic acid disodium salt (6059-S) and its related 1-oxacephems
Journal of Medicinal Chemistry 1979.0
6-(1-Hydroxyalkyl)penam sulfone derivatives as inhibitors of class A and class C β-lactamases II
Bioorganic & Medicinal Chemistry Letters 1999.0
Semisynthetic cephalosporins. Synthesis and structure-activity relations of analogs with 7-acyl groups derived from 2-(cyanomethylthio)acetic acid or 2-[(2,2,2-trifluoroethyl)thio]acetic acid and their sulfoxides and sulfones
Journal of Medicinal Chemistry 1977.0
6-(1-hydroxyalkyl)penam sulfone derivatives as inhibitors of class a and class C β-lactamases I
Bioorganic & Medicinal Chemistry Letters 1999.0
Semisynthetic cephalosporins. Synthesis and structure-activity relations of 7-sulfonylacetamido-3-cephem-4-carboxylic acids
Journal of Medicinal Chemistry 1976.0
Synthesis and antibacterial activity of 2-[(methoxycarbonyl)methylene]cephalosporins
Journal of Medicinal Chemistry 1984.0
Allyl and propargyl substituted penam sulfones as versatile intermediates toward the syntheses of new β-lactamase inhibitors
Bioorganic & Medicinal Chemistry Letters 2001.0
The synthesis and evaluation of 6-alkylidene-2'β-substituted penam sulfones as β-lactamase inhibitors
Bioorganic & Medicinal Chemistry Letters 1999.0