ArticlePloS one2013
The natural product magnolol as a lead structure for the development of potent cannabinoid receptor agonists.
Article in PloS one, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 38 citations in OpenAlex.
- Pharmacology of Non-Psychoactive Phytocannabinoids and Their Potential for Treatment of Cardiometabolic Disease.Handbook of experimental pharmacology · 2025Review
- An integrated in vitro human iPSCs-derived neuron and in vivo animal approach for preclinical screening of anti-seizure compounds.Journal of advanced research · 2024Article
- Magnolol derivatives as specific and noncytotoxic inhibitors of breast cancer resistance protein (BCRP/ABCG2).Bioorganic chemistry · 2024Article
- Structure-Based Virtual Screening and Molecular Dynamics Simulation Assessments of Depsidones as Possible Selective Cannabinoid Receptor Type 2 Agonists.Molecules (Basel, Switzerland) · 2023Article
- In Vitro and In Silico Studies of Neolignans fromMolecules (Basel, Switzerland) · 2023Article
- Efficiency and Mechanism Evaluation ofEvidence-based complementary and alternative medicine : eCAM · 2023Article
- Discovery of a pyrano[2,3-b]pyridine derivative YX-2102 as a cannabinoid receptor 2 agonist for alleviating lung fibrosis.Journal of translational medicine · 2022Article
- Endocannabinoid signaling pathways: beyond CB1R and CB2R.Journal of cell communication and signaling · 2021Review
- Rational approaches for the design of various GABA modulators and their clinical progression.Molecular diversity · 2021Review
- Relevance of Peroxisome Proliferator Activated Receptors in Multitarget Paradigm Associated with the Endocannabinoid System.International journal of molecular sciences · 2021Review
- Pharmacology, Toxicity, Bioavailability, and Formulation of Magnolol: An Update.Frontiers in pharmacology · 2021Review
- Synthesis, characterization, and in vitro evaluation of the selective P2YPurinergic signalling · 2017Article
- Characterization of non-olfactory GPCRs in human sperm with a focus on GPR18.Scientific reports · 2016Article
- Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice.Forensic toxicology · 2016Article
- 4'-O-methylhonokiol increases levels of 2-arachidonoyl glycerol in mouse brain via selective inhibition of its COX-2-mediated oxygenation.Journal of neuroinflammation · 2015Article
- Small Molecules from Nature Targeting G-Protein Coupled Cannabinoid Receptors: Potential Leads for Drug Discovery and Development.Evidence-based complementary and alternative medicine : eCAM · 2015Review
Corrections and comments
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Magnolol (4-allyl-2-(5-allyl-2-hydroxyphenyl)phenol), the main bioactive constituent of the medicinal plant Magnolia officinalis, and its main metabolite tetrahydromagnolol were recently found to activate cannabinoid (CB) receptors. We now investigated the structure-activity relationships of (tetrahydro)magnolol analogs with variations of the alkyl chains and the phenolic groups and could considerably improve potency. Among the most potent compounds were the dual CB1/CB2 full agonist 2-(2-methoxy-5-propyl-phenyl)-4-hexylphenol (61a, K(i) CB1:0.00957 µM; K(i) CB2:0.0238 µM), and the CB2-selective partial agonist 2-(2-hydroxy-5-propylphenyl)-4-pentylphenol (60, K(i) CB1:0.362 µM; K(i ) CB2:0.0371 µM), which showed high selectivity versus GPR18 and GPR55. Compound 61b, an isomer of 61a, was the most potent GPR55 antagonist with an IC50 value of 3.25 µM but was non-selective. The relatively simple structures, which possess no stereocenters, are easily accessible in a four- to five-step synthetic procedure from common starting materials. The central reaction step is the well-elaborated Suzuki-Miyaura cross-coupling reaction, which is suitable for a combinatorial chemistry approach. The scaffold is versatile and may be fine-tuned to obtain a broad range of receptor affinities, selectivities and efficacies.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.