An Overview on Medicinal Chemistry of Synthetic and Natural Derivatives of Cannabidiol.

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Published in Front Pharmacol on June 28, 2017

Authors

Paula Morales1, Patricia H Reggio1, Nadine Jagerovic2

Author Affiliations

1: Department of Chemistry and Biochemistry, University of North Carolina Greensboro, GreensboroNC, United States.
2: Instituto de Química Médica, Consejo Superior de Investigaciones Científicas, Unidad Asociada I+D+i al Instituto de Química Médica/Universidad Rey Juan CarlosMadrid, Spain.

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Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature (1990) 13.60

Molecular characterization of a peripheral receptor for cannabinoids. Nature (1993) 13.45

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Cannabidiol--recent advances. Chem Biodivers (2007) 2.89

GPR55 is a cannabinoid receptor that increases intracellular calcium and inhibits M current. Proc Natl Acad Sci U S A (2008) 2.42

HU-308: a specific agonist for CB(2), a peripheral cannabinoid receptor. Proc Natl Acad Sci U S A (1999) 2.32

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Molecular targets for cannabidiol and its synthetic analogues: effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide. Br J Pharmacol (2001) 2.15

Chemical constituents of marijuana: the complex mixture of natural cannabinoids. Life Sci (2005) 2.13

Cannabidiol in patients with treatment-resistant epilepsy: an open-label interventional trial. Lancet Neurol (2015) 2.07

Peripheral cannabinoid receptor, CB2, regulates bone mass. Proc Natl Acad Sci U S A (2006) 1.95

Lipid G protein-coupled receptor ligand identification using beta-arrestin PathHunter assay. J Biol Chem (2009) 1.91

Cannabidiol displays unexpectedly high potency as an antagonist of CB1 and CB2 receptor agonists in vitro. Br J Pharmacol (2007) 1.85

CB2-receptor stimulation attenuates TNF-alpha-induced human endothelial cell activation, transendothelial migration of monocytes, and monocyte-endothelial adhesion. Am J Physiol Heart Circ Physiol (2007) 1.77

Cannabidiol enhances anandamide signaling and alleviates psychotic symptoms of schizophrenia. Transl Psychiatry (2012) 1.77

The novel endocannabinoid receptor GPR55 is activated by atypical cannabinoids but does not mediate their vasodilator effects. Br J Pharmacol (2007) 1.74

A novel synthetic, nonpsychoactive cannabinoid acid (HU-320) with antiinflammatory properties in murine collagen-induced arthritis. Arthritis Rheum (2004) 1.67

The putative cannabinoid receptor GPR55 affects osteoclast function in vitro and bone mass in vivo. Proc Natl Acad Sci U S A (2009) 1.63

Opposite effects of delta-9-tetrahydrocannabinol and cannabidiol on human brain function and psychopathology. Neuropsychopharmacology (2009) 1.62

Antitumor activity of plant cannabinoids with emphasis on the effect of cannabidiol on human breast carcinoma. J Pharmacol Exp Ther (2006) 1.61

Agonistic properties of cannabidiol at 5-HT1a receptors. Neurochem Res (2005) 1.54

Effects of cannabinoids and cannabinoid-enriched Cannabis extracts on TRP channels and endocannabinoid metabolic enzymes. Br J Pharmacol (2011) 1.53

The isolation and structure of delta-1-tetrahydrocannabinol and other neutral cannabinoids from hashish. J Am Chem Soc (1971) 1.44

Fluorinated Cannabidiol Derivatives: Enhancement of Activity in Mice Models Predictive of Anxiolytic, Antidepressant and Antipsychotic Effects. PLoS One (2016) 1.40

Cannabinoid-2 receptor agonist HU-308 protects against hepatic ischemia/reperfusion injury by attenuating oxidative stress, inflammatory response, and apoptosis. J Leukoc Biol (2007) 1.39

The challenge of atropisomerism in drug discovery. Angew Chem Int Ed Engl (2009) 1.34

Δ(9) -Tetrahydrocannabinol and N-arachidonyl glycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells. Br J Pharmacol (2012) 1.31

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Pathways mediating the effects of cannabidiol on the reduction of breast cancer cell proliferation, invasion, and metastasis. Breast Cancer Res Treat (2010) 1.14

Progress report on new antiepileptic drugs: A summary of the Twelfth Eilat Conference (EILAT XII). Epilepsy Res (2015) 1.14

Antibacterial cannabinoids from Cannabis sativa: a structure-activity study. J Nat Prod (2008) 1.13

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Cannabidiol for neurodegenerative disorders: important new clinical applications for this phytocannabinoid? Br J Clin Pharmacol (2013) 1.08

Meta-analysis of cannabinoid ligand binding affinity and receptor distribution: interspecies differences. Br J Pharmacol (2007) 1.07

Phytocannabinoids beyond the Cannabis plant - do they exist? Br J Pharmacol (2010) 1.03

Cannabidiol in humans-the quest for therapeutic targets. Pharmaceuticals (Basel) (2012) 1.02

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Cannabinoid actions at TRPV channels: effects on TRPV3 and TRPV4 and their potential relevance to gastrointestinal inflammation. Acta Physiol (Oxf) (2011) 1.01

A role for the putative cannabinoid receptor GPR55 in the islets of Langerhans. J Endocrinol (2011) 1.00

Cannabidiol as potential anticancer drug. Br J Clin Pharmacol (2013) 1.00

Enantiomeric cannabinoids: stereospecificity of psychotropic activity. Experientia (1988) 0.99

Cannabidiolic acid as a selective cyclooxygenase-2 inhibitory component in cannabis. Drug Metab Dispos (2008) 0.98

Cannabidiol reduces Aβ-induced neuroinflammation and promotes hippocampal neurogenesis through PPARγ involvement. PLoS One (2011) 0.97

Early phytocannabinoid chemistry to endocannabinoids and beyond. Nat Rev Neurosci (2014) 0.96

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Cannabidiol (CBD) and its analogs: a review of their effects on inflammation. Bioorg Med Chem (2015) 0.95

Antidepressant-like effect of delta9-tetrahydrocannabinol and other cannabinoids isolated from Cannabis sativa L. Pharmacol Biochem Behav (2010) 0.94

Activation of GPR18 by cannabinoid compounds: a tale of biased agonism. Br J Pharmacol (2014) 0.94

Cannabidiol reduces lipopolysaccharide-induced vascular changes and inflammation in the mouse brain: an intravital microscopy study. J Neuroinflammation (2011) 0.94

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New cannabidiol derivatives: synthesis, binding to cannabinoid receptor, and evaluation of their antiinflammatory activity. J Med Chem (2006) 0.88

Synthesis and antitumor activity of quinonoid derivatives of cannabinoids. J Med Chem (2004) 0.87

Characterization of cytochrome P450 3A inactivation by cannabidiol: possible involvement of cannabidiol-hydroxyquinone as a P450 inactivator. Chem Res Toxicol (1998) 0.87

Cannabidiol: an overview of some chemical and pharmacological aspects. Part I: chemical aspects. Chem Phys Lipids (2002) 0.86

Hashish. A simple one-step synthesis of (-)-delta1-tetrahydrocannabinol (THC) from p-mentha-2,8-dien-1-ol and olivetol. J Am Chem Soc (1974) 0.85

Evaluation of the cyclooxygenase inhibiting effects of six major cannabinoids isolated from Cannabis sativa. Biol Pharm Bull (2011) 0.84

Peripheral, but not central effects of cannabidiol derivatives: mediation by CB(1) and unidentified receptors. Neuropharmacology (2005) 0.84

Current Status and Prospects for Cannabidiol Preparations as New Therapeutic Agents. Pharmacotherapy (2016) 0.83

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Cannabidiol-2',6'-dimethyl ether, a cannabidiol derivative, is a highly potent and selective 15-lipoxygenase inhibitor. Drug Metab Dispos (2009) 0.82

Synthesis of a primary metabolite of cannabidiol. Org Lett (2000) 0.81

Cyclohexa-2,5-diene-1,4-dione-based antiproliferative agents: design, synthesis, and cytotoxic evaluation. J Exp Clin Cancer Res (2013) 0.81

Cannabidiol improves lung function and inflammation in mice submitted to LPS-induced acute lung injury. Immunopharmacol Immunotoxicol (2014) 0.81

Cannabidiolic acid, a major cannabinoid in fiber-type cannabis, is an inhibitor of MDA-MB-231 breast cancer cell migration. Toxicol Lett (2012) 0.81

(+)-Cannabidiol analogues which bind cannabinoid receptors but exert peripheral activity only. Eur J Pharmacol (2004) 0.80

HU-446 and HU-465, Derivatives of the Non-psychoactive Cannabinoid Cannabidiol, Decrease the Activation of Encephalitogenic T Cells. Chem Biol Drug Des (2015) 0.80

Enantiomeric cannabidiol derivatives: synthesis and binding to cannabinoid receptors. Org Biomol Chem (2005) 0.80

Antidepressant-like and anxiolytic-like effects of cannabidiol: a chemical compound of Cannabis sativa. CNS Neurol Disord Drug Targets (2014) 0.80

Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics (2015) 0.79

CB2 cannabinoid receptor agonist enantiomers HU-433 and HU-308: An inverse relationship between binding affinity and biological potency. Proc Natl Acad Sci U S A (2015) 0.79

Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes. J Nat Prod (2016) 0.78

Δ(9)-THC and N-arachidonoyl glycine regulate BV-2 microglial morphology and cytokine release plasticity: implications for signaling at GPR18. Front Pharmacol (2014) 0.78

HU-331 is a catalytic inhibitor of topoisomerase IIα. Chem Res Toxicol (2014) 0.78

Evaluation of Serum Cytokines Levels and the Role of Cannabidiol Treatment in Animal Model of Asthma. Mediators Inflamm (2015) 0.78

Anticonvulsant effects of the (-) and (+)isomers of cannabidiol and their dimethylheptyl homologs. Pharmacology (1982) 0.78

Cannabidiol-2',6'-dimethyl ether as an effective protector of 15-lipoxygenase-mediated low-density lipoprotein oxidation in vitro. Biol Pharm Bull (2011) 0.77

Ferruginenes A-C from Rhododendron ferrugineum and their cytotoxic evaluation. J Nat Prod (2011) 0.77

The effect of cannabidiol on ischemia/reperfusion-induced ventricular arrhythmias: the role of adenosine A1 receptors. J Cardiovasc Pharmacol Ther (2014) 0.77

Synthesis and pharmacological evaluation in mice of halogenated cannabidiol derivatives. Chem Pharm Bull (Tokyo) (1999) 0.77

Phytocannabinoids: a unified critical inventory. Nat Prod Rep (2016) 0.77

Antimicrobial and antiparasitic (+)-trans-hexahydrodibenzopyrans and analogues from Machaerium multiflorum. J Nat Prod (2003) 0.77

Cannabielsoin as a new metabolite of cannabidiol in mammals. Pharmacol Biochem Behav (1991) 0.77

The design, synthesis and testing of desoxy-CBD: further evidence for a region of steric interference at the cannabinoid receptor. Life Sci (1995) 0.77

The atypical cannabinoid O-1602: targets, actions, and the central nervous system. Cent Nerv Syst Agents Med Chem (2012) 0.77

Anticonvulsant activity of four oxygenated cannabidiol derivatives. Res Commun Chem Pathol Pharmacol (1975) 0.77

Biotransformation of Cannabidiol to Cannabielsoin by Suspension Cultures of Cannabis sativa and Saccharum officinarum. Planta Med (1983) 0.76