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, 16 (20), 5432-5

1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New High Affinity Ligands for the Cannabinoid CB1 and CB2 Receptors

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1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New High Affinity Ligands for the Cannabinoid CB1 and CB2 Receptors

John W Huffman et al. Bioorg Med Chem Lett.

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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