906803-72-3Relevant academic research and scientific papers
Development of Highly Affine and Selective Fluorinated Cannabinoid Type 2 Receptor Ligands
Moldovan, Rare?-Petru,Hausmann, Kristin,Deuther-Conrad, Winnie,Brust, Peter
supporting information, p. 566 - 571 (2017/05/17)
Cannabinoid type 2 receptors (CB2 receptors) are involved in various pathological processes, and the visualization of their in vivo availability with positron emission tomography (PET) is of high interest. The study focuses on the introduction of fluorine into the structure of the highly affine and selective CB2 receptor ligand N-(adamantan-1-yl)-5-ethyl-2-methyl-1-phenyl-1H-imidazole-4-carboxamide (5). A novel series of compounds was developed by modifying (i) the adamantane-3-position, (ii) the imidazole-N-phenyl ring, and (iii) the imidazole-2-position, and the impact on the CB2 binding affinity and selectivity toward cannabinoid type 1 receptors (CB1) was evaluated. This study identified compound 15 as one of the most potent (Ki(CB2) = 0.29 nM) and selective (CB1/CB2 > 10000) CB2receptor ligands discovered so far, eligible for the development of an18F-labeled PET radiotracer.
Synthesis and SAR of novel imidazoles as potent and selective cannabinoid CB2 receptor antagonists with high binding efficiencies
Lange, Jos H.M.,van der Neut, Martina A.W.,Wals, Henri C.,Kuil, Gijs D.,Borst, Alice J.M.,Mulder, Arie,den Hartog, Arnold P.,Zilaout, Hicham,Goutier, Wouter,van Stuivenberg, Herman H.,van Vliet, Bernard J.
scheme or table, p. 1084 - 1089 (2010/06/11)
The synthesis and structure-activity relationship studies of imidazoles are described. The target compounds 6-20 represent a novel chemotype of potent and CB2/CB1 selective cannabinoid CB2 receptor antagonists/inverse agonists with very high binding efficiencies in combination with favourable log P and calculated polar surface area values. Compound 12 exhibited the highest CB2 receptor affinity (Ki = 1.03 nM) in this series, as well as the highest CB2/CB1 subtype selectivity (>9708-fold).
1H-imidazole derivatives as cannabinoid CB2 receptor modulators
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Page/Page column 13, (2008/06/13)
The invention relates to a group of 1H-imidazole derivatives which are modulators of cannabinoid CB2 receptors, to methods for the preparation of these compounds, to novel intermediates useful for the synthesis of said imidazole derivatives, to methods for the preparation of these intermediates, to pharmaceutical compositions containing one or more of these 1H-imidazole derivatives as active ingredient, as well as to the use of these pharmaceutical compositions for the treatment of disorders in which cannabinoid CB2 receptors are involved. The compounds have the general formula (I) wherein R1-R4 have the meanings given in the specification.
