Synthesis and in vitro evaluation of novel 2-oxo-1,2-dihydroquinoline CB2 receptor inverse agonists

Katri H Raitio; Juha R Savinainen; Tapio Nevalainen; Tomi Järvinen; Jouko Vepsäläinen

doi:10.1111/j.1747-0285.2006.00452.x

Synthesis and in vitro evaluation of novel 2-oxo-1,2-dihydroquinoline CB2 receptor inverse agonists

Chem Biol Drug Des. 2006 Dec;68(6):334-40. doi: 10.1111/j.1747-0285.2006.00452.x.

Authors

Katri H Raitio¹, Juha R Savinainen, Tapio Nevalainen, Tomi Järvinen, Jouko Vepsäläinen

Affiliation

¹ Department of Pharmaceutical Chemistry, University of Kuopio, PO Box 1627, FI-70211 Kuopio, Finland. [email protected]

PMID: 17177896
DOI: 10.1111/j.1747-0285.2006.00452.x

Abstract

Aliphatic amides of 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid 6 were synthesized and evaluated for their CB2 and CB1 receptor activities by a [35S]GTPgammaS membrane-binding assay. Compounds 7-18 produced CB2 inverse agonist activities with a variety of potencies (IC50: 1 nm-1 microm). By contrast, no considerable antagonism of CB1 receptor was observed by 1-10 microm concentrations indicating that synthesized compounds were CB2 receptor selective.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Humans
Hydroxyquinolines / chemical synthesis
Hydroxyquinolines / chemistry*
Hydroxyquinolines / pharmacology*
Mice
Receptor, Cannabinoid, CB1 / antagonists & inhibitors
Receptor, Cannabinoid, CB2 / antagonists & inhibitors*

Substances

Hydroxyquinolines
Receptor, Cannabinoid, CB1
Receptor, Cannabinoid, CB2