Abstract
We here report on the design, synthesis, binding affinities, and fluorescent properties of a series of serotonin 5-HT 1A receptor ligands, with N-[omega-[4-(2-methoxyphenyl)-1-piperazinyl]alkyl]-2-quinolinamine structure. Several of the new ligands displayed nanomolar affinity at 5-HT 1A receptor and good fluorescent properties. In particular, derivative 24 showed a favorable combination of 5-HT 1A receptor affinity ( K i = 0.4 nM), Stokes shift (excitation wavelength = 381 nm, emission wavelength = 455 nm), and quantum yield in ethanol (Phi = 0.45).
MeSH terms
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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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Drug Partial Agonism
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Fluorescent Dyes / chemical synthesis*
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Fluorescent Dyes / chemistry
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Fluorescent Dyes / pharmacology
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Guinea Pigs
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Ileum / drug effects
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Ileum / physiology
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In Vitro Techniques
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Ligands
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Piperazines / chemical synthesis*
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Piperazines / chemistry
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Piperazines / pharmacology
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Quinolines / chemical synthesis*
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Quinolines / chemistry
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Quinolines / pharmacology
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Serotonin 5-HT1 Receptor Agonists*
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Serotonin 5-HT1 Receptor Antagonists
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Structure-Activity Relationship
Substances
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6-amino-N-(2-(4-(2-methoxyphenyl)-1-piperazinyl)butyl)-2-quinolinamine
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Aminoquinolines
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Fluorescent Dyes
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Ligands
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Piperazines
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Quinolines
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Serotonin 5-HT1 Receptor Agonists
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Serotonin 5-HT1 Receptor Antagonists