Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/5767
Title: Synthesis and biological evaluation of New N-alkyl 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides as cannabinoid receptor ligands
Authors: Romano, Silvestri
Alessia, Ligresti
GIUSEPPE LA, Regina
Francesco, Piscitelli
Valerio, Gatti
Antonio, Lavecchia
Pasquini, Serena
Marco, AllarĂ 
Noemi, Fantini
MAURO ANTONIO MARIA, Carai
Chiara, Bigogno
MARCO GIULIO, Rozio
Roberta, Sinisi
Ettore, Novellino
Giancarlo, Colombo
VINCENZO DI, Marzo
Giulio, Dondio
Brizzi, Antonella 
Corelli, Federico 
Keywords: Cannabinoid; Human recombinant CB receptor type 1; Pyrrole bioisoteres; Structure-activity relationships; Pharmacological studies
Issue Date: 2010
Project: None 
Journal: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Abstract: 
A series of N-alkyl 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides were synthesized as new ligands of the human recombinant receptor hCB1. n-Alkyl carboxamides brought out different SARs from the branched subgroup. Unsubstituted pyrrole derivatives bearing a tert-alkyl chain at the 3-carboxamide nitrogen showed greater hCB1 receptor affinity than the corresponding unbranched compounds. In particular, the tert-butyl group as a chain terminal moiety strongly improved hCB1 receptor affinity (compound 24: Ki=45.6 nM; 29: Ki=37.5 nM). Acute administration of either compound 12 or 29 resulted in a specific, dose-dependent reduction in food intake in rats. Such results provide an useful basis for the design of new CB1 ligands.
Description: 
26365
URI: http://hdl.handle.net/20.500.12779/5767
ISSN: 0223-5234
DOI: 10.1016/j.ejmech.2010.09.053
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