132351-68-9

Upstream product

• 17255-67-3 2-(4-bromophenyl)chroman-4-one 
• 65786-14-3 (2E)-3-(4-bromophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 118-93-4 o-hydroxyacetophenone 
• 586-75-4 4-chlorobenzoyl chloride 
• 106129-86-6 1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone 
• 5467-74-3 4-Bromophenylboronic acid 
• 65786-14-3 4-bromo-2'-hydroxylchalcone 
• 1776-08-5 (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 122775-34-2 3-iodo-chromen-4-one 

Downstream Products

• 41255-19-0 2-([1,1′-biphenyl]-4-yl)-4H-chromen-4-one 
• 869559-78-4 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4H-chromen-4-one 
• 1417919-67-5 2-(4'-fluoro-[1,1'-biphenyl]-4-yl)-4H-chromen-4-one 
• 297163-64-5 3-(4-amino-phenyl)-chromen-4-one 

Relevant academic research and scientific papers

Transient and Recyclable Halogenation Coupling (TRHC) for Isoflavonoid Synthesis with Site-Selective Arylation

A transient and recyclable C?H iodination has been designed for the synthesis of isoflavonoids through the domino reactions of o-hydroxyphenyl enaminones and aryl boronic acids in the presence of catalytic KI and Pd catalyst. Instead of the conventional cross-coupling strategy employing pre-halogenated substrates, this method transforms raw C?H bond by means of a transient C?H halogenation to smoothly relay the subsequent C-arylation. Consequently, such a method avoids the pre-functionalization for C?halogen bond installation as well as the generation of stoichiometric halogen-containing waste following the cross-coupled product, disclosing an intriguing new coupling protocol to forge the C?C bond in the virgin area between classical C?X (X=halogen) bond cross coupling and the C?H activation.

Flavones as isosteres of 4(1H)-quinolones: Discovery of ligand efficient and dual stage antimalarial lead compounds

Malaria is responsible for nearly one million deaths annually, and the increasing prevalence of multi-resistant strains of Plasmodium falciparum poses a great challenge to controlling the disease. A diverse set of flavones, isosteric to 4(1H)-quinolones, were prepared and profiled for their antiplasmodial activity against the blood stage of P. falciparum W2 strain, and the liver stage of the rodent parasite Plasmodium berghei. Ligand efficient leads were identified as dual stage antimalarials, suggesting that scaffold optimization may afford potent antiplasmodial compounds.

Oxidative rearrangements of 2'-hydroxychalcones with lh-l-hydroxy-5-methyl- l,2,3-benziodoxathiole 3,3-dioxide

1H-l-hydroxy-5-methyl-l,2,3-benziodoxathiole 3,3-dioxide (HMBI) has been found to effect the direct conversion of 2'-hydroxychalcones with various B-ring substituents to isoflavones in moderate to good yield (34-83%) in methanol under reflux. The reduced byproduct of HMBI is easily recovered by aqueous extraction and can be recycled and reused with high efficiency. Previous reports of conversions of this type required the use of toxic thallium(III) salts or initial protection of the 2'-hydroxyl group.

Structural studies on bioactive compounds. 40.1 synthesis and biological properties of fluoro-, methoxyl-, and amino-substituted 3-phenyl-4H-1-benzopyran-4-ones and a comparison of their antitumor activities with the activities of related 2-phenylbenzothiazoles

A new series of fluoro-, methoxyl-, and amino-substituted isoflavones have been synthesized as potential antitumor agents based on structural similarities to known flavones and isoflavones (quercetin and genistein respectively) and antitumor 2-phenylbenzothiazoles. Target compounds were synthesized using palladium-catalyzed coupling methodologies to construct the central aryl carbon-carbon single bond. The new isoflavone derivatives were tested for in vitro activity in human breast (MDA-MB-468 and MCF-7) and colon (HT29 and HCT-116) cancer cell lines. Low micromolar GI50 values were obtained in a number of cases, with the MDA-MB-468 cell line being the most sensitive overall. Notably, significant potentiation of growth inhibitory activity (GI50 1 μM for 12d, 12f, 12h, 12k, 121, 12o but not the methylene-bridged derivative 12i) was observed when MDA-MB-468 cells were co-incubated with TBDD, a powerful inducer of cytochrome P450 (CYP)-1A1 activity, suggesting that isoflavone derivatives can act as substrates for CYP1A1 bioactivation.

ONE-STEP CONVERSION OF FLAVANONES INTO ISOFLAVANONES: A NEW FACILE BIOMIMETIC SYNTHESIS OF ISOFLAVONES

One-step chemical conversion of flavanones into isoflavones by use of thallium trinitrate (TTN) is reported, and the mechanism of a 2,3-aryl migration in this reaction is discussed in relation to in vivo rearrangement process of flavanone precursors in the isoflavone biosynthesis.