Source:http://linkedlifedata.com/resource/pubmed/id/15715489
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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
4
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pubmed:dateCreated |
2005-2-17
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pubmed:abstractText |
In pursuit of an apparent literature anomaly, S- and R-6-methyl-6,7-dihydro-2H-benzo[a]quinolizin-2-one-3-carboxylic acids (12 and 22) were synthesized by an unambiguous route from optically active norephedrines, and their antibacterial potencies were measured. Against Gram-negative microorganisms and DNA gyrase a preference for S-absolute configuration was found whereas R-absolute stereochemistry was more active against Gram-positives. These results are in partial conflict with an earlier report. In an attempt to enhance potency, racemic 10-fluoro-9-piperazinyl (35) and related analogues were synthesized by a novel route. The latter analogues were surprisingly unimproved in potency. The implications of these findings are briefly discussed.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
Feb
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pubmed:issn |
0022-2623
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
24
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pubmed:volume |
48
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
1229-36
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:15715489-Anti-Bacterial Agents,
pubmed-meshheading:15715489-Binding Sites,
pubmed-meshheading:15715489-DNA Gyrase,
pubmed-meshheading:15715489-Gram-Negative Bacteria,
pubmed-meshheading:15715489-Gram-Positive Bacteria,
pubmed-meshheading:15715489-Piperazines,
pubmed-meshheading:15715489-Quinolizines,
pubmed-meshheading:15715489-Stereoisomerism,
pubmed-meshheading:15715489-Structure-Activity Relationship
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pubmed:year |
2005
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pubmed:articleTitle |
Chiral DNA gyrase inhibitors. 3. Probing the chiral preference of the active site of DNA gyrase. Synthesis of 10-fluoro-6-methyl-6,7-dihydro-9-piperazinyl- 2H-benzo[a]quinolizin-20-one-3-carboxylic acid analogues.
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pubmed:affiliation |
Department of Medicinal Chemistry, University of Kansas, 4010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.,
Research Support, Non-U.S. Gov't
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