The derivatives of the 7-hydroxy-5-oxopyrazolo[4,3-b]pyridine-6-carboxamide scaffold have been reported recently as potent and selective agonists/inverse agonists of the cannabinoid type-2 receptor (CB2R), but the synthetic way adopted has not yet allowed the structure–activity relationship to be fully explored. Herein, we describe a novel synthetic approach based on the use of a 2-tetrahydropyranyl (THP)-protected precursor that opens the way to obtain either N1- or N2-substituted analogs endowed with agonist or inverse agonist activity, respectively, at the CB2 receptor.
Mugnaini, C., Brizzi, A., Vinciarelli, G., Paolino, M., Corelli, F. (2020). New synthesis of N1- and N2-substituted pyrazolo[4,3-b]pyridine-5-one derivatives as CB2 receptor ligands. NEW JOURNAL OF CHEMISTRY, 44(37), 16218-16226 [10.1039/d0nj03400b].
New synthesis of N1- and N2-substituted pyrazolo[4,3-b]pyridine-5-one derivatives as CB2 receptor ligands
Claudia Mugnaini;Antonella Brizzi;Giorgia Vinciarelli;Marco Paolino;Federico Corelli
2020-01-01
Abstract
The derivatives of the 7-hydroxy-5-oxopyrazolo[4,3-b]pyridine-6-carboxamide scaffold have been reported recently as potent and selective agonists/inverse agonists of the cannabinoid type-2 receptor (CB2R), but the synthetic way adopted has not yet allowed the structure–activity relationship to be fully explored. Herein, we describe a novel synthetic approach based on the use of a 2-tetrahydropyranyl (THP)-protected precursor that opens the way to obtain either N1- or N2-substituted analogs endowed with agonist or inverse agonist activity, respectively, at the CB2 receptor.File | Dimensione | Formato | |
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https://hdl.handle.net/11365/1138719