Synthesis and antibacterial activities of optically active ofloxacin.
Two optically active (100% enantiomeric excess) isomers of ofloxacin [(+/-)-ofloxacin; DL-8280; (+/-)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7 H-pyrido[1,2,3-de] [1,4] benzoxazine-6-carboxylic acid] were prepared by use of their optically resolved synthetic intermediates. One of the isomers, (-)-ofloxacin, was 8 to 128 times more potent in inhibiting the multiplication of gram-positive and gram-negative bacteria than the other, (+)-ofloxacin, and approximately two times more active than the racemate, (+/-)-ofloxacin.
Hayakawa
I
I
Atarashi
S
S
Yokohama
S
S
Imamura
M
M
Sakano
K
K
Furukawa
M
M
D055598:Chemical Phenomena; D002627:Chemistry, Physical; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015242:Ofloxacin; D010078:Oxazines / Q000138:chemical synthesis / Q000494:pharmacology*; D013237:Stereoisomerism
D010078:Oxazines; D015242:Ofloxacin