124093-45-4

Upstream product

• 578-57-4 2-bromoanisole 
• 42327-53-7 chrom-3-en-4-ol acetate 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 767-91-9 1-ethynyl-2-methoxybenzene 
• 90-02-8 salicylaldehyde 

Relevant academic research and scientific papers

Development of a new class of aromatase inhibitors: Design, synthesis and inhibitory activity of 3-phenylchroman-4-one (isoflavanone) derivatives

Aromatase (CYP19) catalyzes the aromatization reaction of androgen substrates to estrogens, the last and rate-limiting step in estrogen biosynthesis. Inhibition of aromatase is a new and promising approach to treat hormone-dependent breast cancer. We present here the design and development of isoflavanone derivatives as potential aromatase inhibitors. Structural modifications were performed on the A and B rings of isoflavanones via microwave-assisted, gold-catalyzed annulation reactions of hydroxyaldehydes and alkynes. The in vitro aromatase inhibition of these compounds was determined by fluorescence-based assays utilizing recombinant human aromatase (baculovirus/insect cell-expressed). The compounds 3-(4-phenoxyphenyl)chroman-4- one (1h), 6-methoxy-3-phenylchroman-4-one (2a) and 3-(pyridin-3-yl)chroman-4-one (3b) exhibited potent inhibitory effects against aromatase with IC50 values of 2.4 μM, 0.26 μM and 5.8 μM, respectively. Docking simulations were employed to investigate crucial enzyme/inhibitor interactions such as hydrophobic interactions, hydrogen bonding and heme iron coordination. This report provides useful information on aromatase inhibition and serves as a starting point for the development of new flavonoid aromatase inhibitors.

Palladium-catalyzed direct arylation of 4-chromanones: Selective synthesis of racemic isoflavanones and 3,3-diaryl-4-chromanones

For the first time, the synthesis of racemic isoflavanones has been achieved in satisfactory to good yields and with high selectivity by Pd-catalyzed direct C-3 arylation of 3-unsubstituted 4-chromanones with aryl bromides with the aid of a Pd2(dba)3/tBu 3PHBF4 catalyst system in the presence of KHCO3 as the base in a dioxane/water mixture (4:1). This catalyst system has also been employed in an unprecedented synthesis of 3,3-diaryl-4-chromanones through direct arylation of 4-chromanones in water.

PALLADIUM CATALYSED ARYLATION OF CHROM-3-EN-4-OL ACETATES VIA THEIR TRIBUTYLTIN ENOLATES

Arylation of in situ generated chrom-3-en-4-ol tributyltin enolates with aryl bromide in the presence of a catalytic amount of PdCl22 gives moderate to good yields of the corresponding isoflavanones.