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1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors.
Bioorg Med Chem Lett. 2006 Oct 15; 16(20):5432-5.BM

Abstract

Two series of 1-alkyl-2-aryl-4-(1-naphthoyl)pyrroles were synthesized and their affinities for the cannabinoid CB(1) and CB(2) receptors were determined. In the 2-phenyl series (5) the N-alkyl group was varied from n-propyl to n-heptyl. A second series of 23 1-pentyl-2-aryl-4-(1-naphthoyl)-pyrroles (6) was also prepared. Several compounds in both series have CB(1) receptor affinities in the 6-30nM range. The high affinities of these pyrrole derivatives relative to JWH-030 (1, R=C(5)H(11)) support the hypothesis that these pyrroles interact with the CB(1) receptor primarily by aromatic stacking.

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Authors+Show Affiliations

Huffman JW
Howard L. Hunter Laboratory, Clemson University, Clemson, SC 29634-0973, USA. huffman@clemson.edu
Padgett LW
No affiliation info available
Isherwood ML
No affiliation info available
Wiley JL
No affiliation info available
Martin BR
No affiliation info available

MeSH

Binding, CompetitiveLigandsMolecular StructurePyrrolesReceptor, Cannabinoid, CB1Receptor, Cannabinoid, CB2StereoisomerismStructure-Activity Relationship

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

16889960

Citation

Huffman, John W., et al. "1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New High Affinity Ligands for the Cannabinoid CB1 and CB2 Receptors." Bioorganic & Medicinal Chemistry Letters, vol. 16, no. 20, 2006, pp. 5432-5.
Huffman JW, Padgett LW, Isherwood ML, et al. 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors. Bioorg Med Chem Lett. 2006;16(20):5432-5.
Huffman, J. W., Padgett, L. W., Isherwood, M. L., Wiley, J. L., & Martin, B. R. (2006). 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors. Bioorganic & Medicinal Chemistry Letters, 16(20), 5432-5.
Huffman JW, et al. 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New High Affinity Ligands for the Cannabinoid CB1 and CB2 Receptors. Bioorg Med Chem Lett. 2006 Oct 15;16(20):5432-5. PubMed PMID: 16889960.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors. AU - Huffman,John W, AU - Padgett,Lea W, AU - Isherwood,Matthew L, AU - Wiley,Jenny L, AU - Martin,Billy R, Y1 - 2006/08/04/ PY - 2006/06/12/received PY - 2006/07/17/revised PY - 2006/07/18/accepted PY - 2006/8/8/pubmed PY - 2006/12/9/medline PY - 2006/8/8/entrez SP - 5432 EP - 5 JF - Bioorganic & medicinal chemistry letters JO - Bioorg Med Chem Lett VL - 16 IS - 20 N2 - Two series of 1-alkyl-2-aryl-4-(1-naphthoyl)pyrroles were synthesized and their affinities for the cannabinoid CB(1) and CB(2) receptors were determined. In the 2-phenyl series (5) the N-alkyl group was varied from n-propyl to n-heptyl. A second series of 23 1-pentyl-2-aryl-4-(1-naphthoyl)-pyrroles (6) was also prepared. Several compounds in both series have CB(1) receptor affinities in the 6-30nM range. The high affinities of these pyrrole derivatives relative to JWH-030 (1, R=C(5)H(11)) support the hypothesis that these pyrroles interact with the CB(1) receptor primarily by aromatic stacking. SN - 0960-894X UR - https://www.unboundmedicine.com/medline/citation/16889960/1_Alkyl_2_aryl_4__1_naphthoyl_pyrroles:_new_high_affinity_ligands_for_the_cannabinoid_CB1_and_CB2_receptors_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0960-894X(06)00829-8 DB - PRIME DP - Unbound Medicine ER -
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