Abstract
Ferrocene analogs of known fatty acid amide hydrolase inhibitors and CB2 ligands have been synthesized and characterized spectroscopically and crystallographically. The resulting bio-organometallic isoxazoles were assayed for their effects on CB1 and CB2 receptors as well as on fatty acid amide hydrolase. None had any fatty acid amide hydrolase activity but compound 3, 5-(2-(pentyloxy)phenyl)-N-ferrocenylisoxazole-3-carboxamide, was found to be a potent CB2 ligand (Ki = 32.5 nM).
Keywords:
FAAH; cannabinoids; ferrocene; isoxazole.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amidohydrolases / antagonists & inhibitors
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Amidohydrolases / metabolism
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Binding Sites
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Ferrous Compounds / chemical synthesis
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Ferrous Compounds / chemistry*
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Ferrous Compounds / metabolism
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Humans
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Ligands
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Metallocenes / chemical synthesis
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Metallocenes / chemistry*
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Metallocenes / metabolism
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Molecular Conformation
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Molecular Docking Simulation
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Protein Binding
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Receptor, Cannabinoid, CB1 / chemistry
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Receptor, Cannabinoid, CB1 / metabolism
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Receptor, Cannabinoid, CB2 / chemistry*
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Receptor, Cannabinoid, CB2 / metabolism
Substances
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Ferrous Compounds
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Ligands
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Metallocenes
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Receptor, Cannabinoid, CB1
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Receptor, Cannabinoid, CB2
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Amidohydrolases
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fatty-acid amide hydrolase
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ferrocene