title: 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors.
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.
authors.affiliation: Howard L. Hunter Laboratory, Clemson University, Clemson, SC 29634-0973, USA. huffman@clemson.edu
authors.forename: John W
authors.initials: JW
authors.lastname: Huffman
authors.forename: Lea W
authors.initials: LW
authors.lastname: Padgett
authors.forename: Matthew L
authors.initials: ML
authors.lastname: Isherwood
authors.forename: Jenny L
authors.initials: JL
authors.lastname: Wiley
authors.forename: Billy R
authors.initials: BR
authors.lastname: Martin
mesh_terms: D001667:Binding, Competitive / Q000187:drug effects; D008024:Ligands; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D043884:Receptor, Cannabinoid, CB1 / Q000037:antagonists & inhibitors*; D043885:Receptor, Cannabinoid, CB2 / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D008024:Ligands; D011758:Pyrroles; D043884:Receptor, Cannabinoid, CB1; D043885:Receptor, Cannabinoid, CB2