Abstract
Structure-activity studies have been carried out on a series of imidazo[4,5-f]quinoline derivatives reported to have potent in vivo immunostimulatory activity. This activity has been confirmed, and subtle structure-activity relationships have been uncovered which resulted in the identification of novel analogs (pyrazolo[3,4-f]quinoline derivatives, 7a,b) with potent in vivo effects in a mouse protection model. Regioisomeric pyrazolo[4,3-f]quinoline derivatives (6a,b) were shown to be inactive. Data are presented which support the notion that the in vivo activity is mediated by an immunostimulatory mechanism.
MeSH terms
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Adjuvants, Immunologic / chemical synthesis
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Adjuvants, Immunologic / chemistry*
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Adjuvants, Immunologic / therapeutic use
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Aminoquinolines / chemical synthesis
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Aminoquinolines / chemistry*
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Aminoquinolines / pharmacology
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Animals
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Cattle
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Drug Interactions
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Escherichia coli Infections / drug therapy
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Escherichia coli Infections / immunology
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Female
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Gentamicins / therapeutic use
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Mice
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Molecular Structure
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Pyrazoles / chemical synthesis
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Pyrazoles / chemistry*
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Pyrazoles / pharmacology
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Pyrazoles / therapeutic use
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Quinolines / chemical synthesis
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Quinolines / chemistry*
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Quinolines / therapeutic use
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Structure-Activity Relationship
Substances
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Adjuvants, Immunologic
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Aminoquinolines
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Gentamicins
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Pyrazoles
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Quinolines
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9-((3-methoxyphenyl)amino)-7-methyl-1H-pyrazolo(3,4-f)quinoline