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Synthetic bioactive olivetol-related amides: The influence of the phenolic group in cannabinoid receptor activity.
- Source :
-
Bioorganic & medicinal chemistry [Bioorg Med Chem] 2020 Jun 01; Vol. 28 (11), pp. 115513. Date of Electronic Publication: 2020 Apr 20. - Publication Year :
- 2020
-
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.<br />Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.<br /> (Copyright © 2020 Elsevier Ltd. All rights reserved.)
- Subjects :
- Amides chemical synthesis
Amides chemistry
Analgesics chemical synthesis
Analgesics chemistry
Animals
Cell Line
Dose-Response Relationship, Drug
Humans
Male
Mice
Molecular Structure
Rats
Resorcinols chemistry
Structure-Activity Relationship
TRPV Cation Channels metabolism
Amides pharmacology
Analgesics pharmacology
Receptors, Cannabinoid metabolism
Resorcinols pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3391
- Volume :
- 28
- Issue :
- 11
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 32340793
- Full Text :
- https://doi.org/10.1016/j.bmc.2020.115513