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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
22
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pubmed:dateCreated |
1993-12-10
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pubmed:abstractText |
A series of 1-(2-fluorocyclopropyl)-3-pyridonecarboxylic acids has been prepared. These derivatives are characterized by having a fluorine atom at the 2-position on the cyclopropane ring as the N1 substituent and consist of both cis and trans stereoisomers. Structure-activity relationship studies indicate that the cis derivatives are more potent against Gram-positive bacteria than the corresponding trans counterparts, but the difference in potency against most Gram-negative bacteria is much smaller. The inhibitory effect of compounds 4, 5, 26, 27, 38, and 39 on supercoiling activity of DNA gyrase obtained from E. coli KL-16 correlated with their MICs against the same strain and also depend on their (26, 27, 38, 39) stereochemistry. Introduction of a fluorine atom on the cyclopropyl group resulted in the reduction of lipophilicity compared with the corresponding nonfluorinated quinolones.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
|
pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
Oct
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pubmed:issn |
0022-2623
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pubmed:author | |
pubmed:issnType |
Print
|
pubmed:day |
29
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pubmed:volume |
36
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
|
pubmed:pagination |
3444-8
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:8230135-Anti-Infective Agents,
pubmed-meshheading:8230135-Carboxylic Acids,
pubmed-meshheading:8230135-Fluoroquinolones,
pubmed-meshheading:8230135-Gram-Negative Bacteria,
pubmed-meshheading:8230135-Gram-Positive Bacteria,
pubmed-meshheading:8230135-Microbial Sensitivity Tests,
pubmed-meshheading:8230135-Quinolones,
pubmed-meshheading:8230135-Stereoisomerism,
pubmed-meshheading:8230135-Structure-Activity Relationship
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pubmed:year |
1993
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pubmed:articleTitle |
Fluorocyclopropyl quinolones. 1. Synthesis and structure-activity relationships of 1-(2-fluorocyclopropyl)-3-pyridonecarboxylic acid antibacterial agents.
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pubmed:affiliation |
Research Institute, Daiichi Pharmaceutical Company, Ltd., Tokyo, Japan.
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pubmed:publicationType |
Journal Article,
Comparative Study
|