197587-20-5

Upstream product

• 22972-63-0 α,α-dimethyl-3,5-dimethoxyphenylacetonitrile 
• 120078-30-0 2-(3,5-dimethoxyphenyl)-2-methylpropanal 
• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 941583-81-9 (5-phenoxypentyl)triphenylphosphonium bromide 
• 1605280-98-5 (Z)-3,5-dimethoxy-1-(2-methyl-8-phenoxyoct-3-en-2-yl)benzene 
• 22921-72-8 (5-bromopentoxy)benzene 
• 155586-39-3 (3,5-dimethoxyphenyl)-N-methoxy-N-methylcarboxamide 
• 51795-97-2 6-bromohexyloxybenzene 
• 544-97-8 dimethyl zinc(II) 
• 197587-19-2 1-(3,5-dimethoxyphenyl)-7-phenoxyheptan-1-one 

Downstream Products

• 160512-71-0 5-(8-bromo-2-methyloctan-2-yl)benzene-1,3-diol 
• 197587-22-7 5-(7-Bromo-1,1-dimethyl-heptyl)-2-[(E)-10-(tert-butyl-dimethyl-silanyloxy)-3-difluoromethylene-1-hydroxy-7-methyl-dec-6-enyl]-benzene-1,3-diol 
• 492447-12-8 1-[2-allyloxy-4-(7-bromo-1,1-dimethyl-heptyl)-6-hydroxy-phenyl]-10-(tert-butyl-dimethyl-silanyloxy)-7-methyl-dec-6-en-8-yne-1,3-diol 
• 492447-10-6 1-[2-allyloxy-4-(7-bromo-1,1-dimethyl-heptyl)-6-hydroxy-phenyl]-10-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-7-methyl-dec-6-en-8-yn-1-one 
• 492447-07-1 1-[2-allyloxy-4-(7-bromo-1,1-dimethylheptyl)-6-hydroxyphenyl]ethanone 

Relevant academic research and scientific papers

Novel Functionalized Cannabinoid Receptor Probes: Development of Exceptionally Potent Agonists

We report the development of novel cannabinergic probes that can stabilize the cannabinoid receptors (CBRs) through tight binding interactions. Ligand design involves the introduction of select groups at a judiciously chosen position within the classical

Novel Labelled Cannabinergic Ligands and Related Analogs

Novel cannabinoid ligands represented by the general formulas I, II, and III and methods for preparation and use within which one or more of a fluorescent ligand, nitroxide spin label, metal chelate, biotin moiety, or group with enhanced polarity may be incorporated. The compounds can bind to and modulate the cannabinoid CB1 and CB2 receptors and thereby considered specific ligands for these receptors. Some of the disclosed compounds that bind to cannabinoid CB1 and CB2 receptors can exhibit tight or irreversible binding characteristics for these receptors. Due to the presence of the imaging/diagnostic and/or therapeutic functional groups including fluorescent groups, nitroxide spin labels, metal chelates, biotin moieties, and groups with enhanced polarity, the disclosed compounds may be useful as imaging/diagnostic tools and/or therapeutic agents.

Highly Selective, Amine-Derived Cannabinoid Receptor 2 Probes

The endocannabinoid (eCB) system is implied in various human diseases ranging from central nervous system to autoimmune disorders. Cannabinoid receptor 2 (CB2R) is an integral component of the eCB system. Yet, the downstream effects elicited by this G protein-coupled receptor upon binding of endogenous or synthetic ligands are insufficiently understood—likely due to the limited arsenal of reliable biological and chemical tools. Herein, we report the design and synthesis of CB2R-selective cannabinoids along with their in vitro pharmacological characterization (binding and functional studies). They combine structural features of HU-308 and AM841 to give chimeric ligands that emerge as potent CB2R agonists with high selectivity over the closely related cannabinoid receptor 1 (CB1R). The synthesis work includes convenient preparation of substituted resorcinols often found in cannabinoids. The utility of the synthetic cannabinoids in this study is showcased by preparation of the most selective high-affinity fluorescent probe for CB2R to date.

Crystal structures of agonist-bound human cannabinoid receptor CB 1

The cannabinoid receptor 1 (CB 1) is the principal target of the psychoactive constituent of marijuana, the partial agonist " 9 -tetrahydrocannabinol (Δ9 -THC). Here we report two agonist-bound crystal structures of human CB 1 in complex with a tetrahydro

2-CYCLOALKYL RESORCINOL CANNABINERGIC LIGANDS

The present invention relates to novel 2-cycloalkyl resorcinol compounds; to pharmaceutical compositions comprising the compounds; and to methods of preparing the compounds and uses thereof. The disclosed compounds can bind to and modulate the cannabinoid

Synthesis of covalent probes for the radiolabeling of the cannabinoid receptor

The main psychoactive constituent of marijuana, (-)-Α9-tetrahydrocannabinol, produces most of its physiological effects by interacting with the CB1 cannabinoid receptor, a membrane protein belonging to the large superfamily of G-protein coupled receptors. The 3-D structure of the receptor binding site is of value in the design of novel medications for a variety of therapeutic indications. To obtain information on the amino acid residues associated with this binding site, we have designed and synthesized a cannabinergic CB1 ligand prototype carrying an electrophilic isothiocyanato group capable of reacting covalently with amino acid residues bearing thiol or unprotonated amino groups. The ligand also incorporates an iodide atom, which can serve as a high-activity radiolabel. The key step in our synthesis involves a rapid intramolecular Diels-Alder reaction of a transiently formed o-quinone methide, which proceeds stereospecifically with the formation of the tricyclic cannabinoid template. Introduction of the iodo group is the last step in the sequence and is compatible with the use of 125I-radiolabel.

Synthesis of a bifunctional cannabinoid ligand

A novel bifunctional classical-nonclassical hybrid cannabinoid has been prepared expeditiously through the Diels-Alder reaction of an ortho-quinomethane.