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Synthesis and SAR studies of 2-oxoquinoline derivatives as CB2 receptor inverse agonists.
J Med Chem. 2006 Mar 23; 49(6):2022-7.JM

Abstract

The highly CB2 selective cannabinoid receptor inverse agonist, 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid N-benzo[1,3]dioxol-5-ylmethyl)amide (JTE-907; 9b), served as the lead compound for investigating the structure-activity relationships of its analogues and in the search for more potent and effective CB2 receptor inverse agonists. A series of aromatic amides of 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid 6 was synthesized, and the CB2 receptor activities of the compounds were determined by a [35S]GTPgammaS-binding assay using membranes of CHO cells stably transfected with the human CB2 receptor. As a result, all the compounds were defined as full CB2 receptor inverse agonists, and additionally, except for two 3,4-dihydroxyphenylalkylamides, they were found to be equally potent as SR144528.

Authors+Show Affiliations

Department of Pharmaceutical Chemistry, University of Kuopio, P.O. Box 1627, FI-70211 Kuopio, Finland. Katri.Raitio@uku.fiNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Comparative Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16539390

Citation

Raitio, Katri H., et al. "Synthesis and SAR Studies of 2-oxoquinoline Derivatives as CB2 Receptor Inverse Agonists." Journal of Medicinal Chemistry, vol. 49, no. 6, 2006, pp. 2022-7.
Raitio KH, Savinainen JR, Vepsäläinen J, et al. Synthesis and SAR studies of 2-oxoquinoline derivatives as CB2 receptor inverse agonists. J Med Chem. 2006;49(6):2022-7.
Raitio, K. H., Savinainen, J. R., Vepsäläinen, J., Laitinen, J. T., Poso, A., Järvinen, T., & Nevalainen, T. (2006). Synthesis and SAR studies of 2-oxoquinoline derivatives as CB2 receptor inverse agonists. Journal of Medicinal Chemistry, 49(6), 2022-7.
Raitio KH, et al. Synthesis and SAR Studies of 2-oxoquinoline Derivatives as CB2 Receptor Inverse Agonists. J Med Chem. 2006 Mar 23;49(6):2022-7. PubMed PMID: 16539390.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and SAR studies of 2-oxoquinoline derivatives as CB2 receptor inverse agonists. AU - Raitio,Katri H, AU - Savinainen,Juha R, AU - Vepsäläinen,Jouko, AU - Laitinen,Jarmo T, AU - Poso,Antti, AU - Järvinen,Tomi, AU - Nevalainen,Tapio, PY - 2006/3/17/pubmed PY - 2006/4/29/medline PY - 2006/3/17/entrez SP - 2022 EP - 7 JF - Journal of medicinal chemistry JO - J Med Chem VL - 49 IS - 6 N2 - The highly CB2 selective cannabinoid receptor inverse agonist, 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid N-benzo[1,3]dioxol-5-ylmethyl)amide (JTE-907; 9b), served as the lead compound for investigating the structure-activity relationships of its analogues and in the search for more potent and effective CB2 receptor inverse agonists. A series of aromatic amides of 7-methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid 6 was synthesized, and the CB2 receptor activities of the compounds were determined by a [35S]GTPgammaS-binding assay using membranes of CHO cells stably transfected with the human CB2 receptor. As a result, all the compounds were defined as full CB2 receptor inverse agonists, and additionally, except for two 3,4-dihydroxyphenylalkylamides, they were found to be equally potent as SR144528. SN - 0022-2623 UR - https://www.unboundmedicine.com/medline/citation/16539390/Synthesis_and_SAR_studies_of_2_oxoquinoline_derivatives_as_CB2_receptor_inverse_agonists_ L2 - https://doi.org/10.1021/jm050879z DB - PRIME DP - Unbound Medicine ER -