157766-27-3Relevant articles and documents
7-Oxo-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamides as Selective CB 2 cannabinoid receptor ligands: Structural investigations around a novel class of full agonists
Baraldi, Pier Giovanni,Saponaro, Giulia,Moorman, Allan R.,Romagnoli, Romeo,Preti, Delia,Baraldi, Stefania,Ruggiero, Emanuela,Varani, Katia,Targa, Martina,Vincenzi, Fabrizio,Borea, Pier Andrea,Aghazadeh Tabrizi, Mojgan
experimental part, p. 6608 - 6623 (2012/09/22)
Cannabinoid receptor agonists have gained attention as potential therapeutic targets of inflammatory and neuropathic pain. Here, we report the identification and optimization of a series of 7-oxo-[1,4]oxazino[2,3,4-ij] quinoline-6-carboxamide derivatives as a novel chemotype of selective cannabinoid CB2 receptor agonists. Structural modifications led to the identification of several compounds as potent and selective cannabinoid receptor agonists (20, hCB2Ki = 2.5 nM, SI = 166; 21, hCB2Ki = 0.81 nM, SI = 383; 38, hCB2K i = 15.8 nM, SI > 633; 56, hCB2Ki = 8.12 nM, SI > 1231; (R)-58, hCB2Ki = 9.24 nM, SI > 1082). The effect of a chiral center on the biological activity was also investigated, and it was found that the (R)-enantiomers exhibited greater affinity at the CB2 receptor than the (S)-enantiomers. In 3,5-cyclic adenosine monophosphate assays, the novel series behaved as agonists, exhibiting functional activity at the human CB2 receptor.
Process for the preparation of polyhalogenated benzotrifluorides, benzotrichlorides and benzoyl chlorides and new trihalogenobenzotrichlorides and -benzoyl chlorides
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, (2008/06/13)
Polyhalogenated benzotrifluorides can be reacted with chlorides from the series of Friedel-Crafts catalysts to give the corresponding benzotrichlorides, which can be hydrolysed by water in the presence of iron(III) chloride to give the corresponding benzoyl chlorides. These are suitable as intermediate products for the preparation of active compounds for medicaments and feed additives.
