1: J Med Chem. 2007 Nov 1;50(22):5471-5484. Epub 2007 Oct 4.

Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class
of Potent CB(2)-Selective Cannabinoid Receptor Ligands: Consequences in Receptor 
Affinity and Functionality.

Stern E, Muccioli GG, Bosier B, Hamtiaux L, Millet R, Poupaert JH, Hénichart JP, 
Depreux P, Goossens JF, Lambert DM.

Institut de Chimie Pharmaceutique Albert Lespagnol, Université de Lille 2, EA
2692, 3 rue du Pr. Laguesse, B.P. 83, F-59006 Lille, France, Unité de Chimie
Pharmaceutique et de Radiopharmacie, Ecole de Pharmacie, Faculté de Médecine,
Université catholique de Louvain, 73 avenue E. Mounier UCL-CMFA (7340), B-1200
Bruxelles, Belgium, and Laboratoire de Chimie Analytique, EA 4034, Faculté des
Sciences Pharmaceutiques et Biologiques, Université de Lille 2, 3 rue du Pr.
Laguesse, B.P. 83, F-59006 Lille, France.

CB2 receptor selective ligands are becoming increasingly attractive drugs due to 
the potential role of this receptor in several physiopathological processes.
Thus, the development of our previously described series of
4-oxo-1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further
characterize the structure-affinity and structure-functionality relationships of 
these derivatives. The influence of the side chain was investigated by
synthesizing compounds bearing various carboxamido and keto substituents. On the 
other hand, the role of the quinoline central scaffold was studied by
synthesizing several 6-, 7-, or 8-chloro-4-oxo-1,4-dihydroquinolines, as well as 
4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The
effect of these modifications on the affinity and functionality at the CB2
receptor was studied and allowed for the characterization of new selective CB2
receptor ligands.

PMID: 17915849 [PubMed - as supplied by publisher]

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