42327-64-0

Upstream product

• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 536-74-3 phenylacetylene 
• 140870-45-7 3-Benzenesulfonyl-6-methoxy-chroman-4-one 
• 140870-42-4 6-Methoxy-3-phenylsulfanyl-chroman-4-one 
• 140870-49-1 3-Benzenesulfonyl-6-methoxy-3-phenyl-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.

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.