42079-81-2

Usage

InChI:InChI=1/C15H8Br2O2/c16-10-6-11-13(18)8-14(9-4-2-1-3-5-9)19-15(11)12(17)7-10/h1-8H

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 1214-47-7 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one 
• 98-88-4 benzoyl chloride 
• 6425-08-7 4,4'-(phenylmethylene)bismorpholine 
• 15482-67-4 3',5'-dibromo-2'-hydroxychalcone 
• 22362-66-9 3,5-dibromo-2-hydroxyacetophenone 

Relevant academic research and scientific papers

Site-Selective Suzuki-Miyaura Reaction of 6,8-Dibromoflavone

8-Aryl- and 6,8-diarylflavones were prepared by Suzuki-Miyaura reactions of 6,8-dibromoflavone. In spite of the greater steric hindrance, the first attack proceeded with good site selectivity at position 8.

Ferrocenyl flavonoid-induced morphological modifications of endothelial cells and cytotoxicity against B16 murine melanoma cells

With the aim of improving the cytotoxic and vascular disrupting activities of flavonoids, several classes of ferrocenyl-modified flavonoids were prepared and tested on cancer and endothelial cells. Three ten-member series of ferrocenyl flavonoids: chalcones ((E)-1-(R-2′-hydroxyphenyl)-3- ferrocenylprop-2-en-1-ones), aurones ((Z)-R-2-(ferrocenylidene)benzofuran-3- ones) and flavones (R-2-ferrocenyl-chromen-4-ones) were synthesized by recently reported methods. Three ferrocenyl flavonols (R-3-hydroxy-2-ferrocenyl-chromen- 4-ones) and four ferrocenyl flavanones (3-ferrocenylmethylidenyl-R-2- phenylchroman-4-ones) were also obtained. All compounds were evaluated for their cytotoxic effects on a cancer cell line (B16 murine melanoma) and for their morphological effects on endothelial cells (EAhy 926). Some interesting structure-activity relationships were disclosed: of all the compounds, the halogen-substituted aurones showed the best cytotoxic activity, with IC 50 values ranging between 12 and 18 μM. Ferrocenyl flavonols and ferrocenyl flavanones with substitution in the 3-position (-OH and C-Fc respectively) were not active against cancer or endothelial cells. Some of the ferrocenyl flavones caused the endothelial cells to adopt a round shape ("rounding up") at submicromolar concentrations, which can be predictive of vascular disrupting activity. The most morphologically active flavones showed only moderate cytotoxicity against cancer cells, indicating that they may primarily act as antivascular agents.

Synthesis of 2,3,6,8-tetrasubstituted chromone scaffolds

A useful and efficient synthetic strategy to 2,3,6,8-tetrasubstituted chromone derivatives has been developed. 2-Aryl/styryl-8-bromo-6-chloro-3- hydroxychromone derivatives were synthesized and used as scaffolds by introducing a variety of substituents in

New flavones by a novel synthetic route

Twelve new flavones (3) were prepared by the reaction of 2-hydroxy-α- bromoacetophenones (1) with piperidine or morpholine aminals of benzaldeydes (2) in refluxing methanol. The products (3) were fully characterised by 1H NMR and IR spectroscopy and MS spectrometry.