(2,3)-alpha-Methylenepenams: synthesis and in vitro activity.
A series of alpha-methylene penicillins was synthesized and SAR were studied. The alpha-isomers were found to be chemically reactive and biologically active in contrast to the beta-isomers. In addition, the alpha-isomers have broader spectrum of in vitro activity than the corresponding penicillins. Generally, the alpha-isomers are more active against gram-negative bacteria than the corresponding penicillins, but slightly weaker in potency towards gram-positive organisms.
Wei
C C
CC
Roche Research Center, Nutley, NJ 07110.
Luk
K C
KC
West
K F
KF
Roberts
J L
JL
Pruess
D
D
Moore
D W
DW
Yang
R
R
Steppe
T
T
Rossman
P
P
Weigele
M
M
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001426:Bacterial Proteins; D002352:Carrier Proteins / Q000378:metabolism; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006602:Hexosyltransferases; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D002267:Muramoylpentapeptide Carboxypeptidase / Q000378:metabolism; D010400:Penicillin G / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D046915:Penicillin-Binding Proteins; D010406:Penicillins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010458:Peptidyl Transferases; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D001426:Bacterial Proteins; D002352:Carrier Proteins; D046915:Penicillin-Binding Proteins; D010406:Penicillins; C054982:2,3-methylene penam; D010458:Peptidyl Transferases; D006602:Hexosyltransferases; D002267:Muramoylpentapeptide Carboxypeptidase; D010400:Penicillin G