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N-치환 Piperazino Ciprofloxacin 誘導體의 合成 및 抗菌作用
任哲夫,韓完植 중앙대학교 약학연구소 1993 약학 논총 Vol.7 No.-
In order to find more potent antimicrobial agents, fourteen new 1-clyclo-propyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(N-substituted)-1-piperazinyl]-3-quinoline carboxylic acid derivatives(R=methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, phenyl, 2,4-dimethoxy phenyl) and their pivaloyloxymethyl esters were synthesized and evaluated for their antimirobial activities. Treatment of isocynates with 1-cyclopropyl-6-fluoro-1,4-digydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid[Ciprofloxacin]afforded N-substitued carbamoyl piperazino quinoline carboxylic [acids(1)-(8)]. Their pivaloyloxymethyl esters were obtained by the reaction of N-substitued ciprofloxacins with pivaloyloxymethyl chloride in the presence of potassium carbonate and potassium iodide[(9)-(14)]. The synthesized compounds were examined their antimicrobial activities in vitro against Streptococus pyogenes 77 A, Streptococcus faecium MD 8, b, Staphylococcus aureus SG 511, Escherichia coli 1507 E, Pseudomonas aeruginosa 1711 M, Pseudomonas aeruginosa 1592 E, Salmonella typhimurium, Klebsiella oxytoca 1082 E, Klebsiel la aerogenes 1522 E, Enterobacter cloacae 1321 E. 1. The most active compound [12], 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(N-isopropyl carbamoyl)-1-piperazinyl]-3-quinoline, carboxylic acid pivaloyoxymethyl ester, exhibited the growth inhibitory activity at a concentration of 0.5㎍/ml against St.pyogenes 77 A, 1.0㎍/ml against St.faecium MD 8b, 1.0㎍/ml against Staphylococcus aureus SG 511, 0.06㎍/ml against Escherichia coli 1507 E, 0.25㎍/ml aginst Peudomanas aeruginosa 1711 M, 0.25㎍/ml against Pseudomonas aeruginosa 1592 E, 0.25㎍/ml against Salmonella typhimurium, 0.06㎍/ml against Klebsiella oxytoca 1082 E, 0.06㎍/ml against Klebsiella aerogenes 1522 E, 0.25㎍/ml against Enterobacter cloacae 1321 E. 2. Most synthesized carbamoyl piperazino ciprofloxacins showed more potent antimicrobial activities than those their pivaloyloxymethyl esters.
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