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.
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|Titolo:||Synthesis and biological evaluation of New N-alkyl 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides as cannabinoid receptor ligands|
|Rivista:||EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY|
|Citazione:||Romano, S., Alessia, L., GIUSEPPE LA, R., Francesco, P., Valerio, G., Antonio, L., et al. (2010). Synthesis and biological evaluation of New N-alkyl 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides as cannabinoid receptor ligands. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 45(12), 5878-5886.|
|Appare nelle tipologie:||1.1 Articolo in rivista|