105705-48-4

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 42327-53-7 chrom-3-en-4-ol acetate 
• 1621-58-5 3-(4-methoxyphenyl)-4H-chromen-4-one 
• 90-02-8 salicylaldehyde 
• 768-60-5 4-methoxyphenylacetylen 
• 611-20-1 salicylonitrile 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 100-66-3 methoxybenzene 
• 139449-21-1 3-phenylthio-2,3-dihydro-(4H)-benzopyran-4-one 
• 1776-09-6 3-bromochroman-4-one 
• 153488-86-9 3-(allyloxycarbonyl)chroman-4-one 
• 18649-43-9 4-methoxyphenyllead(IV) triacetate 
• 824-94-2 p-methoxybenzyl chloride 
• 79744-47-1 1-(2-hydroxyphenyl)-2-(4-methoxyphenyl)ethanone 

Downstream Products

• 1621-58-5 3-(4-methoxyphenyl)-4H-chromen-4-one 
• 145917-96-0 3-(4-methoxyphenyl)-2H-chromene 

Relevant academic research and scientific papers

Enantioselective construction of sterically hindered tertiary α-aryl ketones: A catalytic asymmetric synthesis of isoflavanones

A method for the catalytic asymmetric α-arylation of ketones bearing very sterically hindered aryl rings has been developed. This reaction occurs under mild conditions, in short reaction times and has been applied to the first catalytic asymmetric synthesis of isoflavanones.

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.

Gold(I)-catalyzed annulation of salicylaldehydes and aryl acetylenes as an expedient route to isoflavanones

(Chemical Equation Presented) The value of gold 'n' rings: An isoflavanone moiety is the key structural feature of many complex natural products. It is now shown that such structures can be generated efficiently and atom economically by the annulation of

Rapid syntheses of (±)-pterocarpans and isoflavones via the gold-catalyzed annulation of aldehydes and alkynes

(±)-Pterocarpan and analogues (4a-c) have been synthesized efficiently via the annulation of salicylaldehydes (1a, 1b and 1c) and o-methoxymethoxylphenylacetylene (2a), followed by a one-pot reduction and acidic cyclization of the ketones (3a-c). In addition, isoflavone derivatives (5a-c) have been synthesized rapidly, in two steps, via the annulation of salicylaldehyde (1a) and arylacetylenes (2b, 2c and 2d), followed by IBX/DMSO oxidation of the isoflavanones (3d, 3e and 3f).

Inhibitors of acyl CoA:cholesterol acyltransferase

Conformational restriction of previously disclosed acyclic diphenylethyl)diphenylacetamides led to the discovery of several potent inhibitors of acyl CoA:cholesterol acyltransferase (ACAT). cis-[2-(4- Hydroxyphenyl)-1-indanyl]diphenylacetamide (4a) was the most potent ACAT inhibitor identified (IC50 = 0.04 μM in an in vitro rat hepatic microsomal ACAT assay, ED50 = 0.72 mg/kg/day in cholesterol-fed hamsters).

Aryllead mediated synthesis of isoflavanone and isoflavone derivatives

The reaction of aryllead (IV) triacetates with 3-(phenylthio)-chroman-4-one and 2-p-methoxyphenyl-3-(phenylthio)-chroman-4-one derivatives was carried out in chloroform in presence of pyridine to afford moderate to quantitative yields of the corresponding hindered 3-aryl-3-phenylthiochroman-4-one derivatives. Removal of the phenylthio group by oxidation with dimethyldioxirane led to the corresponding isoflavones and 2-p-methoxyphenylisoflavones, and by reduction with a large excess of nickel boride to the isoflavanones and 2-(4′-anisyl)-isoflavanones respectively. In the 2-p-methoxyphenyl series the nickel boride reduction of the compounds bearing ortho-substituted 3-aryl groups gave the chalcones which were recyclised under basic catalysis.

Organolead-mediated Arylation of Allyl β-Ketoesters: A Selective Synthesis of Isoflavanones and Isoflavones

Arylation of A-ring substituted and unsabstituted 3-allyloxycarbonylchroman-4-ones with aryllead(IV) triacetates followed by selective catalytic deallyloxycarbonylation affords isoflavanones or isoflavones in high overall yields.The highest yield in the arylation step was observed in the reaction of 5,7-dimethoxychroman-4-one with the more hindered 2,4,6-trimethoxyphenyllead triacetate.

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.