Synthetic bioactive olivetol-related amides: The influence of the phenolic group in cannabinoid receptor activity
Articolo
Data di Pubblicazione:
2020
Citazione:
Synthetic bioactive olivetol-related amides: The influence of the phenolic group in cannabinoid receptor activity / A. Brizzi, F. Aiello, S. Boccella, M.G. Cascio, L. De Petrocellis, M. Frosini, F. Gado, A. Ligresti, L. Luongo, P. Marini, C. Mugnaini, F. Pessina, F. Corelli, S. Maione, C. Manera, R.G. Pertwee, V. Di Marzo. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - 28:11(2020 Jun 01), pp. 115513.1-115513.11. [10.1016/j.bmc.2020.115513]
Abstract:
Focusing on the importance of the free phenolic hydroxyl moiety, a family of 23 alkylresorcinol-based compounds were developed and evaluated for their cannabinoid receptor binding properties. The non-symmetrical hexylresorcinol derivative 29 turned out to be a CB2-selective competitive antagonist/inverse agonist endowed with good potency. Both the olivetol- and 5-(2-methyloctan-2-yl)resorcinol-based derivatives 23 and 24 exhibited a significant antinociceptive activity. Interestingly, compound 24 proved to be able to activate both cannabinoid and TRPV1 receptors. Even if cannabinoid receptor subtype selectivity remained a goal only partially achieved, results confirm the validity of the alkylresorcinol nucleus as skeleton for the identification of potent cannabinoid receptor modulators.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Alkylresorcinols; Antinociceptive effect; Cannabinoid ligands; Dual ligand; Endocannabinoids; Transient receptor potential vanilloid type-1 channel; Amides; Analgesics; Animals; Cell Line; Dose-Response Relationship, Drug; Humans; Male; Mice; Molecular Structure; Rats; Receptors, Cannabinoid; Resorcinols; Structure-Activity Relationship; TRPV Cation Channels
Elenco autori:
A. Brizzi, F. Aiello, S. Boccella, M.G. Cascio, L. De Petrocellis, M. Frosini, F. Gado, A. Ligresti, L. Luongo, P. Marini, C. Mugnaini, F. Pessina, F. Corelli, S. Maione, C. Manera, R.G. Pertwee, V. Di Marzo
Link alla scheda completa: