73323-63-4Relevant articles and documents
Synthesis, pharmacological evaluation and docking studies of pyrrole structure-based CB2 receptor antagonists
Ragusa, Giulio,Gómez-Ca?as, María,Morales, Paula,Hurst, Dow P.,Deligia, Francesco,Pazos, Ruth,Pinna, Gerard A.,Fernández-Ruiz, Javier,Goya, Pilar,Reggio, Patricia H.,Jagerovic, Nadine,García-Arencibia, Moisés,Murineddu, Gabriele
, p. 651 - 667 (2015/08/04)
Abstract During the last years, there has been a continuous interest in the development of cannabinoid receptor ligands that may serve as therapeutic agents and/or as experimental tools. This prompted us to design and synthesize analogues of the CB2 receptor antagonist N-fenchyl-5-(4-chloro-3-methyl-phenyl)-1-(4-methyl-benzyl)-1H-pyrazole-3-carboxamide (SR144528). The structural modifications involved the bioisosteric replacement of the pyrazole ring by a pyrrole ring and variations on the amine carbamoyl substituents. Two of these compounds, the fenchyl pyrrole analogue 6 and the myrtanyl derivative 10, showed high affinity (Ki in the low nM range) and selectivity for the CB2 receptor and both resulted to be antagonists/inverse agonists in [35S]-GTPγS binding analysis and in an in vitro CB2 receptor bioassay. Cannabinoid receptor binding data of the series allowed identifying steric constraints within the CB2 binding pocket using a study of Van der Waals' volume maps. Glide docking studies revealed that all docked compounds bind in the same region of the CB2 receptor inactive state model.
Photocyclization of 1-(1-Chloroisoquinolin-6-yl)-1H-v-triazolopyridines to 10-Chloro-5H-pyridopyrroloisoquinolines (Azaellipticines)
Rivalle, Christian,Ducrocq, Claire,Lhoste, Jean-Marc,Bisagni, Emile
, p. 2176 - 2180 (2007/10/02)
Whereas thermal cyclization of 1-(5,8-dimethyl-1-oxo-1,2-dihydroisoquinolin-6-yl)-1H-v-triazolopyridine affords 6,11-dimethyl-5H-pyridopyrroloisoquinolin-10(9H)-one which cannot be chlorinated to the corresponding chloro derivativ