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    Synthesis of N-phenyl-N-(3-(piperidin-1-yl)propyl)benzofuran-2-carboxamides as new selective ligands for sigma receptors

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    Author
    Marriott, Karla-Sue C.
    Morrisson, Andrew Z.
    Moore, Misty
    Olubajo, Olarongbe
    Stewart, Leonard E.
    Affiliation
    Savannah State University
    Keyword
    sigma receptors
    ligand
    benzofuran
    carboxamide
    organic chemistry
    Issue Date
    2012-12
    Type
    Article
    Language
    en
    Metadata
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    URI
    http://hdl.handle.net/11286/581761
    Abstract
    Novel benzofuran-2-carboxamide ligands, which are selective for sigma receptors, have been synthesized via a microwave-assisted Perkin rearrangement reaction and a modified Finkelstein halogen-exchange used to facilitate N-alkylation. The ligands synthesized are the 3-methyl-N-phenyl-N-(3-(piperidin-1-yl)propyl)benzofuran-2-carboxamides (KSCM-1, KSCM-5 and KSCM-11). The benzofuran-2-carboxamide structure was N-arylated and N-alkylated to include both N-phenyl and N-(3-(piperidin-1-yl)propyl substituents, respectively. These new carboxamides exhibit high affinity at the sigma-1 receptor with Ki values ranging from 7.8 to 34 nM. Ligand KSCM-1 with two methoxy substituents at C-5 and C-6 of the benzofuran ring, and Ki = 27.5 nM at sigma-1 was found to be more selective for sigma-1 over sigma-2.
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