[Studies on quinolone antibacterials. I. Synthesis and antibacterial activity of 7-(2-aminoethoxy)-, 7-(2-aminoethylthio)-, and 7-(2-aminoethylamino)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo qui noline -3-carboxylic acids and their derivatives].
7-(2-Aminoethoxy)-, 7-(2-aminoethylthio)-, and 7-(2-aminoethylamino)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoq uin oline-3- carboxylic acids and their derivatives (11a--f, h, j, k, 12a--f, and 13a--f) were synthesized and their antibacterial activities were tested. Among them, compounds (13a, d) having a primary amino group at the terminal position of alkoxy and alkylthio groups were found to have excellent in vitro and in vivo antibacterial activity comparable to those of ciprofloxacin (5). Structure-activity relationship of these compounds was also stated.
Central Research Laboratories, Hokuriku Seiyaku Co., Ltd., Fukui, Japan.
T
T
Yoshida
Y
Y
Yamamoto
N
N
Yagi
S
S
Yasuda
H
H
Katoh
Y
Y
Itoh
D000818:Animals; D000890:Anti-Infective Agents; D001419:Bacteria / Q000187:drug effects*; D002939:Ciprofloxacin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use; D004352:Drug Resistance, Microbial; D004927:Escherichia coli Infections / Q000188:drug therapy; D024841:Fluoroquinolones; D008297:Male; D051379:Mice; D013329:Structure-Activity Relationship
D000890:Anti-Infective Agents; D024841:Fluoroquinolones; C054029:ciprofloxacin-7-ethylenediamine; C065111:7-(2-aminoethoxy)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid; C065112:7-(2-aminoethylthio)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid; D002939:Ciprofloxacin