Abstract
Weak partial agonists that promote a desensitized state of the α7 nicotinic acetylcholine receptor (nAChR) have been associated with anti-inflammatory effects. Exemplar compounds feature a tertiary or quaternary ammonium group. We report the synthesis, structure, and electrophysiological evaluation of 1-ethyl-4-phenylthiomorpholin-1-ium triflate, a weak partial agonist with a sulfonium isostere of the ammonium pharmacophore. These results offer new insights in understanding nAChR-ligand interactions and provide a new chemical space to target the α7 nAChR.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Ammonium Compounds / chemical synthesis
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Ammonium Compounds / chemistry
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Ammonium Compounds / pharmacology
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Animals
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Humans
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Models, Molecular
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Morpholines / chemical synthesis
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Morpholines / chemistry*
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Morpholines / pharmacology*
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Nicotinic Agonists / chemical synthesis
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Nicotinic Agonists / chemistry*
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Nicotinic Agonists / pharmacology*
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Onium Compounds / chemical synthesis
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Onium Compounds / chemistry*
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Onium Compounds / pharmacology*
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Sulfonium Compounds / chemical synthesis
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Sulfonium Compounds / chemistry*
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Sulfonium Compounds / pharmacology*
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Xenopus laevis
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alpha7 Nicotinic Acetylcholine Receptor / agonists*
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alpha7 Nicotinic Acetylcholine Receptor / metabolism
Substances
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1-ethyl-4-phenylthiomorpholin-1-ium
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Ammonium Compounds
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Morpholines
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Nicotinic Agonists
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Onium Compounds
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Sulfonium Compounds
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alpha7 Nicotinic Acetylcholine Receptor