Semisynthetic beta-lactam antibiotics. I. Synthesis and antibacterial activity of new ureidopenicillin derivatives having catechol moieties.
The synthesis and antibacterial activity of new ureidopenicillin derivatives having catechol moieties in the 6-acyl side chain are described. These compounds showed remarkably strong activities against Pseudomonas aeruginosa. Especially, 6-[(R)-2-[3-(3,4-dihydroxybenzoyl)-3-methyl-1-ureido]-2- phenylacetamido]penicillanic acid (7a) had the most potent activity in vitro against Gram-negative bacteria, its activity being 30 approximately 60-fold greater than that of piperacillin against most strains of P. aeruginosa.
Ohi
N
N
Aoki
B
B
Shinozaki
T
T
Moro
K
K
Noto
T
T
Nehashi
T
T
Okazaki
H
H
Matsunaga
I
I
D000818:Animals; D001424:Bacterial Infections / Q000188:drug therapy; D002396:Catechols / Q000494:pharmacology; D008297:Male; D051379:Mice; D008815:Mice, Inbred Strains; D010406:Penicillins / Q000138:chemical synthesis* / Q000494:pharmacology; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013329:Structure-Activity Relationship
D002396:Catechols; D010406:Penicillins; C034221:catechol