Synthesis of N-phenyl-N-(3-(piperidin-1-yl)propyl)benzofuran-2-carboxamides as new selective ligands for sigma receptors
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Authors
Marriott, Karla-Sue C.
Morrisson, Andrew Z.
Moore, Misty
Olubajo, Olarongbe
Stewart, Leonard E.
Advisors
Department
Savannah State University
Keywords
sigma receptors
ligand
benzofuran
carboxamide
organic chemistry
ligand
benzofuran
carboxamide
organic chemistry
Issue Date
2012-12
Type
Article
Language
en
Description
Other Titles
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.