106009-51-2

Upstream product

• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 98-88-4 benzoyl chloride 

Downstream Products

• 447451-05-0 7-benzoyl-5-O-prenyl chrysin 
• 1577233-41-0 5-O-(ethoxycarbonyl)methyl-7-O-benzoyl chrysin 
• 33554-47-1 5-O-Methylchrysin 

Relevant academic research and scientific papers

Synthesis and antitumor activity evaluation of chrysin derivatives

A series of 5,7-disubstituted chrysin, 7-monosubstituted chrysin, 5-monosubstituted chrysin derivatives were synthesized by alkylation, acetylation, benzoylation, carboxymethylation, and evaluated on their antitumor activity of H22 cells in the search for potential antitumor agents. Among them, compound 3 (5,7-diacetyl chrysin) displayed the most potent antitumor activity with IC50 value of 141 μM. Moreover, there is significant up-regulation of G2 in cell cycle of H22.

Synthesis of chrysin derivatives and screening of antitumor activity

A series of aromatic or long-chain chrysin derivatives (1–10) were synthesized by esterification of chrysin and acyl chloride. The chemical structures of these compounds were determined by mass spectrum (MS), 1H NMR, and 13C NMR spec

Flavonoid-based inhibitors of the Phi-class glutathione transferase from black-grass to combat multiple herbicide resistance

The evolution and growth of multiple-herbicide resistance (MHR) in grass weeds continues to threaten global cereal production. While various processes can contribute to resistance, earlier work has identified the phi class glutathione-S-transferase (AmGSTF1) as a functional biomarker of MHR in black-grass (Alopecurus myosuroides). This study provides further insights into the role of AmGSTF1 in MHR using a combination of chemical and structural biology. Crystal structures of wild-type AmGSTF1, together with two specifically designed variants that allowed the co-crystal structure determination with glutathione and a glutathione adduct of the AmGSTF1 inhibitor 4-chloro-7-nitro-benzofurazan (NBD-Cl) were obtained. These studies demonstrated that the inhibitory activity of NBD-Cl was associated with the occlusion of the active site and the impediment of substrate binding. A search for other selective inhibitors of AmGSTF1, using ligand-fishing experiments, identified a number of flavonoids as potential ligands. Subsequent experiments using black-grass extracts discovered a specific flavonoid as a natural ligand of the recombinant enzyme. A series of related synthetic flavonoids was prepared and their binding to AmGSTF1 was investigated showing a high affinity for derivatives bearing a O-5-decyl-α-carboxylate. Molecular modelling based on high-resolution crystal structures allowed a binding pose to be defined which explained flavonoid binding specificity. Crucially, high binding affinity was linked to a reversal of the herbicide resistance phenotype in MHR black-grass. Collectively, these results present a nature-inspired new lead for the development of herbicide synergists to counteract MHR in weeds. This journal is

Regioselective syntheses of 6-(1,1-dimethylallyl)- and 8-(3,3-dimethylallyl) chrysins

The first regioselective syntheses of 6-(1,1-dimethylallyl)- and 8-(3,3-dimethylallyl) chrysins have been designed. Claisen rearrangement of protected 5-O-(3,3-dimethylallyl) chrysin in N,N-diethylaniline at 200-217°C gave selective access to the 8-(3,3-dimethylallyl) isomer. Similar rearrangement in N,N-diethylbutylamine at 140-160°C, or in cycloheptane/Eu(fod)3 at 100°C, led to the formation of the 6-(1,1-dimethylallyl) isomer. Four different protecting groups for position 7 of chrysin have been compared, and found to follow the order of interest Bz>MOM>TBDPS>MEM.