1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New high affinity ligands for the cannabinoid CB1 and CB2 receptors
Huffman, JW., Padgett, LW., Isherwood, ML., Wiley, J., & Martin, BR. (2006). 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New high affinity ligands for the cannabinoid CB1 and CB2 receptors. Bioorganic and Medicinal Chemistry Letters, 16(20), 5432-5435.
Two series of 1-alkyl-2-aryl-4-(1-naphthoyl)pyrroles were synthesized and their affinities for the cannabinoid CB, and CB2 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, receptor affinities in the 6-30 nM range. The high affinities of these pyrrole derivatives relative to JWH-030 (1,R = C5H11) support the hypothesis that these pyrroles interact with the CB, receptor primarily by aromatic stacking. (c) 2006 Elsevier Ltd. All rights reserved