ChemInform Abstract: 2‐Styrylchromones: Biological Action, Synthesis, and Reactivity

Abstract

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Characterisation of (E)‐2‐styrylchromones by electrospray ionisation mass spectrometry: singular gas‐phase formation of benzoxanthenones

“…( E )‐2‐Styrylchromones were synthesised by a three‐step sequence starting from 2'‐hydroxyacetophenone and the appropriate cinnamoyl chloride, commercially available in the case of 1 or prepared in situ from cinnamic acids and phosphoryl chloride for 1a–c [9c]. The 12 H ‐benzo[12 a ]xanthen‐12‐one 21 was prepared according to a literature procedure involving the irradiation of ( E )‐2‐styryl‐4 H ‐chromen‐4‐one ( 1 ) with a high‐pressure Hg lamp at room temperature .…”

“…They are known to present anti‐allergic, antitumor,[1b,4] antiviral, anti‐oxidant, and anti‐inflammatory properties and also for their use as antagonists of A 3 adenosine receptor . In view of the important biological activities described in the literature for this family of compounds, 2‐styrylchromones represent a rather important substrate and have been used in numerous transformations …”

“…2‐Styrylchromones are chromone derivatives that possess a styryl group in the 2‐position of the chromone moiety and can be readily available by simple and efficient synthetic transformations in a good overall yield using, for example, an aldol condensation/oxidative cyclisation[9a,f,10] or a Baker‐Venkataraman rearrangement [9a,c,f,11]…”

Anti-inflammatory potential of 2-styrylchromones regarding their interference with arachidonic acid metabolic pathways

“…In a recent theoretical study [34], a correlation was found between the lipoxygenase inhibitory activity of flavonoid molecules and their planar character, which probably facilitates the access, through a hydrophobic cavity, to the catalytic site of the enzyme. Considering this rationale, the planar character of 2-SC [16,29,35], conferred by the styryl link between the B-ring and the C-ring, may contribute to their effectiveness as 5-LOX inhibitors.…”

“…The first step involves the O-acylation of appropriate 2 0 -hydroxyacetophenones with cinnamoyl chloride derivatives to give 2 0 -cinnamoyloxyacetophenones. These intermediates were converted into 5-aryl-3-hydroxy-1-(2-hydroxyaryl)-2,4-pentadien-1-ones by the base-catalysed Baker-Venkataraman rearran- gement [27][28][29]. The cyclodehydration of these b-diketones with a mixture of DMSO and a catalytic amount of iodine or ptoluenesulfonic acid gives polybenzyloxy-2-SC, which were debenzylated by treatment with hydrogen bromide in acetic acid at reflux, to give the expected hydroxy-2-SC 1A-1D, 2A-2D and 3A-3D.…”