PYRIDONECARBOXYLIC ACIDS AS ANTIBACTERIAL AGENTS .4. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 7-(3-AMINO-1-PYRROLIDINYL)-1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID AND ITS ANALOGS

被引：84
|
作者：
EGAWA, H [1 ]
MIYAMOTO, T [1 ]
MINAMIDA, A [1 ]
NISHIMURA, Y [1 ]
OKADA, H [1 ]
UNO, H [1 ]
MATSUMOTO, J [1 ]
机构：
[1] DAINIPPON PHARMACEUT CO LTD, RES LABS, ENOKI 33-94, SUITA, OSAKA 564, JAPAN
来源：
JOURNAL OF MEDICINAL CHEMISTRY | 1984年 / 27卷 / 12期
关键词：
D O I：
10.1021/jm00378a004
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The title compounds with an amino- and/or hydroxyl-substituted cyclic group at C-7 were prepared with 1-substituted 7-chloro, 7-(ethylsulfonyl)- and 7-(tosyloxy)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids and their ethyl esters with cyclic amines such as 3-aminopyrrolidine. The N-1 substituent includes ethyl, vinyl and 2-fluoroethyl groups. As a result of in vitro and in vivo antibacterial screenings [Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa], 3 compounds, 1-ethyl- and 1-vinyl-7-(3-amino-1-pyrrolidinyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids and 1-vinyl-7-[3-(methylamino)-1-pyrrolidinyl]analog were more active than enoxacin and worthy of further biological study. Structure-activity relationships are discussed.
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页码：1543 / 1548
页数：6
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