1: J Med Chem. 2006 Jan 12;49(1):70-9. 

Novel 4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives as new CB2
cannabinoid receptors agonists: synthesis, pharmacological properties and
molecular modeling.

Stern E, Muccioli GG, Millet R, Goossens JF, Farce A, Chavatte P, Poupaert JH,
Lambert DM, Depreux P, Henichart JP.

Institut de Chimie Pharmaceutique Albert Lespagnol, Universite de Lille 2, EA
2692, 3 rue du Pr. Laguesse, B.P. 83, F-59006 Lille, France.

Recent data indicated that the CB(2) cannabinoid receptor constitutes an
attractive drug target due to its potential functional role in several
physiological and pathological processes. A set of
4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives, characterized by the
presence of some important structural requirements exhibited by other classes of
cannabinoid ligands, such as an aliphatic or aromatic carboxamide group in
position 3, and an alkyl or benzyl group in position 1, was synthesized and
assayed to measure their respective affinity for both human CB(1) and CB(2)
cannabinoid receptors. The results indicate that these 3-carboxamido-quinolones
derivatives exhibited a CB(2) receptor selectivity, particularly derivatives
28-30, and 32R. Moreover, in the [(35)S]-GTPgammaS binding assay, all the
compounds behaved as CB(2) receptor agonists. Molecular modeling studies showed
that compound 30 interacts with the CB(2) receptor through a combination of
hydrogen bond and aromatic/hydrophobic interactions. In conclusion,
4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives constitute a new class of
potent and selective CB(2) cannabinoid receptors agonists.

PMID: 16392793 [PubMed - indexed for MEDLINE]