140870-50-4

Upstream product

• 140870-47-9 3-Benzenesulfonyl-6-methyl-3-phenyl-chroman-4-one 
• 39513-75-2 6-methyl-4-chromanone 
• 108-86-1 bromobenzene 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 536-74-3 phenylacetylene 
• 139449-22-2 3-Benzenesulfonyl-6-methyl-chroman-4-one 
• 139449-20-0 6-Methyl-3-phenylsulfanyl-chroman-4-one 

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.

Ligand Coupling Route to Isoflavanones and Isoflavones

Phenylation of 3-phenylsulfonylchroman-4-ones using Ph3BiCO3 leading to the synthesis of isoflavanones and isoflavones is reported.