Synthesis and antibacterial activity of some novel 6-methyl- and 6-propenyl-substituted carbapenems.
The synthesis and antibacterial activity of a number of 6-methyl- and 6-propenyl-substituted carbapenems is described. The 6-(hydroxymethyl)- and 6-(aminomethyl)carbapenems possessed more potent antibacterial activity in vitro than their respective 6-(1'(R)-hydroxyethyl) or 6-(1'(R)-aminoethyl) counterparts. However, because of reduced stability, the 6-(aminomethyl)carbapenem was found to be inactive in vivo. All 6-hydroxypropenyl or 6-aminopropenyl derivatives that were prepared were less active than their respective 6-heteroethyl-substituted analogues.
Mastalerz
H
H
Bristol-Myers Squibb Pharmaceutical Research Institute, Candiac, Quebec, Canada.
Menard
M
M
Ruediger
E
E
Fung-Tomc
J
J
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D001419:Bacteria / Q000187:drug effects; D015780:Carbapenems / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D004355:Drug Stability; D004927:Escherichia coli Infections / Q000188:drug therapy; D051379:Mice; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D015780:Carbapenems