RT Journal Article
T1 Novel sulfenamides and sulfonamides based on pyridazinone and pyridazine scaffolds as CB1 receptor ligand antagonists
A1 Murineddu, Gabriele
A1 Deligia, Francesco
A1 Ragusa, Giulio
A1 García Toscano, Laura
A1 Gómez Cañas, María
A1 Asproni, Battistina
A1 Satta, Valentina
A1 Cichero, Elena
A1 Pazos, Ruth
A1 Fossa, Paola
A1 Loriga, Giovanni
A1 Fernández Ruiz, José Javier
A1 Pinna, Gerard A.
AB A series of sulfenamide and sulfonamide derivatives was synthesized and evaluated for the affinity at CB1 and CB2 receptors. The N-bornyl-S-(5,6-di-p-tolylpyridazin-3-yl)-sulfenamide, compound 11, displayed good affinity and high selectivity for CB1 receptors (Ki values of 44.6 nM for CB1 receptors and >40 μM for CB2 receptors, respectively). The N-isopinocampheyl-sulfenamide 12 and its sulfonamide analogue 22 showed similar selectivity for CB1 receptors with Ki values of 75.5 and 73.2 nM, respectively. These novel compounds behave as antagonists/inverse agonists at CB1 receptor in the [35S]-GTPγS binding assays, and none showed adequate predictive blood–brain barrier permeation, exhibiting low estimated LD50. However, testing compound 12 in a supraspinal analgesic test (hot-plate) revealed that it was as effective as the classic CB1 receptor antagonist rimonabant, in reversing the analgesic effect of a cannabinoid agonist.
PB Elsevier
SN 0968-0896
YR 2018
FD 2018-01
LK https://hdl.handle.net/20.500.14352/131205
UL https://hdl.handle.net/20.500.14352/131205
LA eng
NO Murineddu G, Deligia F, Ragusa G, García-Toscano L, Gómez-Cañas M, Asproni B, et al. Novel sulfenamides and sulfonamides based on pyridazinone and pyridazine scaffolds as CB1 receptor ligand antagonists. Bioorganic & Medicinal Chemistry 2018;26:295–307. https://doi.org/10.1016/j.bmc.2017.11.051
DS Docta Complutense
RD 30 mar 2026