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Closed Access item Structural-activity relationship study on C-4 carbon atom of the CB1 antagonist SR141716: synthesis and pharmacological evaluation of 1,2,4-triazole-3-carboxamides

Authors:Jagerovic, Nadine
Hernandez-Folgado, Laura
Alkorta, Ibon
Goya Laza, Pilar
Martín, María Isabel
Dannert, María Teresa
Alsasua, Ángela
Frigola, Jordi
Cuberes, María Rosa
Dordal, Alberto
Holenz, Jörg
Keywords:1,2,4-Triazole, Cannabinoid, Mouse vas deferens, SR141716
Issue Date:Jan-2006
Citation:European Journal of Medicinal Chemistry 41 : 114–120 (2006)
Abstract:A series of 1,2,4-triazole-3-carboxamides has been prepared from alkyl-1,2,4-triazole-3-carboxylates under mild conditions. The ability of these triazoles to displace [3H]-CP55940 from CB1 cannabinoid receptor was measured. However, they showed only poor to moderate binding affinities, indicating that substitution of the C-4 pyrazole atom of the CB1 reference compound SR141716 by a nitrogen atom results in loss of affinity. Further investigations for functionality indicated that the compound 6a exhibited significant cannabinoid antagonistic properties in the mouse vas deferens functional assay. This leads us to the conclusion that 6a binds at a different CB1 binding site or at a new cannabinoid receptor subtype.
Publisher version (URL):http://dx.doi.org/10.1016/j.ejmech.2005.06.012
Appears in Collections:(IQM) Artículos

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