42327-60-6

Upstream product

• 90-02-8 salicylaldehyde 
• 766-97-2 4-n-methylphenylacetylene 
• 58113-12-5 3-(4-methylphenyl)-4H-chromen-4-one 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 153488-86-9 3-(allyloxycarbonyl)chroman-4-one 
• 3076-56-0 p-tolyllead triacetate 
• 153488-90-5 3-allyloxycarbonyl-3-(4-methylphenyl)chroman-4-one 
• 106-38-7 para-bromotoluene 
• 42327-53-7 chrom-3-en-4-ol acetate 

Downstream Products

• 58113-12-5 3-(4-methylphenyl)-4H-chromen-4-one 

Relevant academic research and scientific papers

NOVEL SUBSTITUTED N, N-DIMETHYLAMINOALKYL ETHERS OF ISOFLAVANONE OXIMES AS Η1-RECEPTOR ANTAGONISTS

The present invention relates to compounds of formula (I), and salts thereof and the pharmaceutical composition containing them in treatment of various diseases, as allergic rhinitis where R1 and R2 are, independently, hydrogen, halogen, C1_3 alkyl or C1-3alkoxy; R3 is phenyl optionally substituted by R4 and R5 which are, independently hydrogen, halogen, C1-3 alkyl, C1-3-alkoxy, fluoro-, difluoro- and trifluoromethyl, nitrile group, N,N-diC1-3alkyl- amide, carboC1-3 alkoxy or C1-3alkylsulphone groups; R3 is pyridyl group containing nitrogen at various positions in the benzene ring, n is one of the integers 1 or 2.

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.

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).

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.