The synthesis and antibacterial activities of quinolones containing five- and six-membered heterocyclic substituents at the 7-position.
A series of 6-fluoro-7-substituted-1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids were prepared. The substituents at the 7-position included five- and six-membered heterocyclic rings such as oxazoline and oxazine as well as five-membered heteroaromatic rings such as oxazoles and imidazoles. The structure--activity relationships (SAR) of these compounds indicated that oxazole substituents containing a 2-methyl group had the greatest in vitro potency. The compounds showed greater in vitro antibacterial activity against Gram-positive organisms than against Gram-negative organisms.
Cooper
C S
CS
Anti-Infective Research Division, Abbott Laboratories, Abbott Park, Illinois 60064.
Klock
P L
PL
Chu
D T
DT
Fernandes
P B
PB
D042462:4-Quinolones; D000890:Anti-Infective Agents / Q000138:chemical synthesis*; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship
D042462:4-Quinolones; D000890:Anti-Infective Agents; D006571:Heterocyclic Compounds