81325-86-2Relevant academic research and scientific papers
Synthesis of chlorinated flavonoids with anti-inflammatory and pro-apoptotic activities in human neutrophils
Freitas, Marisa,Ribeiro, Daniela,Tomé, Sara M.,Silva, Artur M.S.,Fernandes, Eduarda
, p. 153 - 164 (2014/09/29)
Neutrophils are considered the central cells of acute inflammation. Flavonoids have been suggested as therapeutic agents to avoid damages induced by inflammatory processes. It is well known the reactivity of flavonoids with hypochlorous acid produced by neutrophils, to form stable mono and dichlorinated products. In this study, we synthesized novel chlorinated flavonoids and investigated their effect in neutrophils' oxidative burst and in its lifespan, in comparison with the parent non-chlorinated flavonoids. The obtained results demonstrate that chlorinated flavonoids were more efficient than their parent compounds in modulating neutrophils' oxidative burst in phorbol myristate acetate-activated neutrophils. Some of the tested flavonoids drive neutrophil apoptosis in a caspase 3-dependent fashion. The present data showed that 8-chloro-3′,4′,5,7-tetrahydroxyflavone (4a) constitute an alternative anti-inflammatory therapy, due to the proven ability to suppress mechanisms engaged at the onset and progression of inflammation.
Nitration, Amination, and Halogenation of Di-O-methylphloracetophenone
Acton, John P.,Donnelly, Dorothy J.,Donnelly, John A.
, p. 73 - 80 (2007/10/02)
Chlorination of the title compound gave 5'- and 3'-chloro-2'-hydroxy-4',6'-dimethoxyacetophenone.The nitration of its acetate, followed successively by reduction, diazotization, and reaction with cuprous chloride, gave the 3'-substituted series, 2'-acetoxy-4',6'-dimethoxy-3'-nitroacetophenone, 3'-amino-2'-hydroxy-4',6'-dimethoxyacetophenone, and 3'-chloro-2'-hydroxy-4',6'-methoxyacetophenone, respectively.The orientation of substituents in the products was proved.The amino and chloro members of the isomeric 5'-substituted series were available via 2'-hydroxy-4',6'-dimethoxy-5'-phenylazoacetophenone, the product of the reaction of the title compound with benzenediazonium chloride. - Keywords: Acetophenone; Aromatic substitution; Nuclear regioselectivity
