The synthesis and evaluation of 6-alkylidene-2'beta-substituted penam sulfones as beta-lactamase inhibitors.
Penicillin sulfones, which structurally incorporate both a 6-position alkylidene substituent and a 2'beta substituent, have been synthesized and evaluated as inhibitors of class C and class A serine beta-lactamases. Incorporation of the 2'beta-substituent generally improves inhibitory activity. Substituents that improve transport across the bacterial cell membrane have also been incorporated.
Buynak
J D
JD
Department of Chemistry, Southern Methodist University, Dallas, TX 75275-0314, USA.
Rao
A S
AS
Doppalapudi
V R
VR
Adam
G
G
Petersen
P J
PJ
Nidamarthy
S D
SD
D003023:Cloxacillin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D004359:Drug Therapy, Combination / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D010403:Penicillin Resistance; D010878:Piperacillin / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013450:Sulfones / Q000737:chemistry; D065093:beta-Lactamase Inhibitors; D001618:beta-Lactamases
D004791:Enzyme Inhibitors; D013450:Sulfones; D065093:beta-Lactamase Inhibitors; D001618:beta-Lactamases; C034413:beta-lactamase TEM-1; D003023:Cloxacillin; D010878:Piperacillin