5330-66-5Relevant articles and documents
Synthesis, Crystal Structure, and Biological Activity of 4-phenoxyacetyl-substituted methyl-3,4-dihydro-2H-1,4-benzoxazine
Kang, Tao,Liu, Cheng-Guo,Qu, Hai-Tao
, p. 259 - 264 (2021/08/03)
Two novel substituted benzoxazine derivatives have been synthesized through reduction, cyclization, and acylation reactions. The target compounds were characterized by IR, 1H-NMR, 13C-NMR, and HRMS. The single-crystal structures of t
Chemoenzymatic Asymmetric Synthesis of 1,4-Benzoxazine Derivatives: Application in the Synthesis of a Levofloxacin Precursor
López-Iglesias, María,Busto, Eduardo,Gotor, Vicente,Gotor-Fernández, Vicente
, p. 3815 - 3824 (2015/05/04)
A versatile and general route has been developed for the asymmetric synthesis of a wide family of 3-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazines bearing different pattern substitutions in the aromatic ring. Whereas hydrolases were not suitable for resoluti
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.
