6 alpha-hydroxypenicillanic acid-S(S)-oxide and analogues: synthesis and antimicrobial activity.
The synthesis and in vitro antibacterial activity of a series of 6-oxygenated penicillanic acid sulfoxides is described. 6 alpha-Hydroxypenicillanic acid-S(S)-oxide (1a) exhibits weak Gram-negative antibacterial activity and appears to be similar to amdinocillin (5) in its mode of action. 6 alpha-Hydroxypenicillanic acid-S(R)-oxide (4a) has a broader spectrum of activity, but again is rather weak. The corresponding 6 beta-hydroxy series is essentially devoid of activity.
Roberts
J L
JL
Roche Research Center, Hoffmann-La Roche Inc., Nutley, New Jersey 07110.
Bevilacqua
P F
PF
Keith
D D
DD
Pawson
B A
BA
Pruess
D L
DL
Rossman
P L
PL
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects*; D010397:Penicillanic Acid / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D010397:Penicillanic Acid