Studies on beta-lactam antibiotics. VII. Effect on antibacterial activity of the oxime O-substituents with various functional groups in the 7 beta-[(Z)-2-(2-amino-4-thiazolyl)-2-oxyiminoacetamido]cephalosporins.
The synthesis and in vitro activity of the 7-[O-substituted oxyiminoacetamido]cephalosporins (I) without substitution at 3-position of a cephem nucleus are described. Effect of changing the oxime O-substituents (R1) with various functional groups in the 7-acyl residue on antibacterial activity was examined. Against Gram-positive bacteria, cephems with hydrophilic functions in the R1 moiety such as hydroxyethyl, aminoethyl and carboxymethyl groups showed decrease of the activity, while cephems with lipophilic functions such as cyanomethyl, methylthiomethyl and halogenoethyl groups exhibited increase of the activity. However, influence of the substituents (R1) on activity against Gram-negative bacteria was observed to be relatively independent of the nature of their functional groups.
D002511:Cephalosporins / Q000096:biosynthesis / Q000633:toxicity*; D004926:Escherichia coli / Q000187:drug effects; D007202:Indicators and Reagents; D007711:Klebsiella pneumoniae / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D011513:Proteus mirabilis / Q000187:drug effects; D011514:Proteus vulgaris / Q000187:drug effects; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
D002511:Cephalosporins; D007202:Indicators and Reagents