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

2.50
Hdl Handle:
http://hdl.handle.net/11286/581761
Title:
Synthesis of N-phenyl-N-(3-(piperidin-1-yl)propyl)benzofuran-2-carboxamides as new selective ligands for sigma receptors
Authors:
Marriott, Karla-Sue C.; Morrisson, Andrew Z.; Moore, Misty; Olubajo, Olarongbe; Stewart, Leonard E.
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.
Affiliation:
Savannah State University
Citation:
Marriott, K. C., Morrison, A. Z., Moore, M., Olubajo, O., & Stewart, L. E. (2012). Synthesis of N-phenyl-N-(3-(piperidin-1-yl)propyl)benzofuran-2-carboxamides as new selective ligands for sigma receptors. Bioorganic & Medicinal Chemistry, 206856-6861. doi:10.1016/j.bmc.2012.09.044
Journal:
Bioorganic & Medicinal Chemistry
Issue Date:
Dec-2012
URI:
http://hdl.handle.net/11286/581761
DOI:
doi:10.1016/j.bmc.2012.09.044
Additional Links:
http://www.ncbi.nlm.nih.gov/pubmed/23084435
Type:
Article
Language:
en
Sponsors:
DA027086/DA/NIDA NIH HHS/United States HHSN-271-2008-00025-C/PHS HHS/United States R03 DA027086/DA/NIDA NIH HHS/United States
Appears in Collections:
Faculty Research Articles

Full metadata record

DC FieldValue Language
dc.contributor.authorMarriott, Karla-Sue C.en
dc.contributor.authorMorrisson, Andrew Z.en
dc.contributor.authorMoore, Mistyen
dc.contributor.authorOlubajo, Olarongbeen
dc.contributor.authorStewart, Leonard E.en
dc.date.accessioned2015-11-04T22:09:39Zen
dc.date.available2015-11-04T22:09:39Zen
dc.date.issued2012-12en
dc.identifier.citationMarriott, K. C., Morrison, A. Z., Moore, M., Olubajo, O., & Stewart, L. E. (2012). Synthesis of N-phenyl-N-(3-(piperidin-1-yl)propyl)benzofuran-2-carboxamides as new selective ligands for sigma receptors. Bioorganic & Medicinal Chemistry, 206856-6861. doi:10.1016/j.bmc.2012.09.044en
dc.identifier.doidoi:10.1016/j.bmc.2012.09.044en
dc.identifier.urihttp://hdl.handle.net/11286/581761en
dc.description.abstractNovel 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.en
dc.description.sponsorshipDA027086/DA/NIDA NIH HHS/United States HHSN-271-2008-00025-C/PHS HHS/United States R03 DA027086/DA/NIDA NIH HHS/United Statesen
dc.language.isoenen
dc.relation.urlhttp://www.ncbi.nlm.nih.gov/pubmed/23084435en
dc.subjectsigma receptorsen
dc.subjectliganden
dc.subjectbenzofuranen
dc.subjectcarboxamideen
dc.subjectorganic chemistryen
dc.titleSynthesis of N-phenyl-N-(3-(piperidin-1-yl)propyl)benzofuran-2-carboxamides as new selective ligands for sigma receptorsen
dc.typeArticleen
dc.contributor.departmentSavannah State Universityen
dc.identifier.journalBioorganic & Medicinal Chemistryen
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