58113-12-5

Basic information

• Product Name: 3-(4-methylphenyl)-4H-chromen-4-one
• Synonyms: 3-(4-methylphenyl)-4H-chromen-4-one
• CAS NO: 58113-12-5
• Molecular Weight: 236.27
• Mol File: 58113-12-5.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 3-(4-methylphenyl)-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-methylphenyl)-4H-chromen-4-one(58113-12-5)
• EPA Substance Registry System: 3-(4-methylphenyl)-4H-chromen-4-one(58113-12-5)

Safety Data

• Hazardous Substances Data: 58113-12-5(Hazardous Substances Data)

Upstream product

• 49619-82-1 3-bromo-4H-chromen-4-one 
• 5720-05-8 4-methylphenylboronic acid 
• 89839-87-2 2-(4-methylphenyl)-2,3-dihydro-4H-chromen-4-one 
• 122775-34-2 3-iodo-chromen-4-one 
• 5142-75-6 tri(p-tolyl)bismuth 
• 34000-27-6 (2E)-1-(2-hydroxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one 
• 118-93-4 o-hydroxyacetophenone 
• 31614-66-1 tributyl(p-tolyl)stannane 
• 106129-86-6 1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone 
• 1776-08-5 (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 13400-26-5 3-hydroxychromen-4-one 
• 491-38-3 1-benzopyran-4(4H)-one 
• 1258792-31-2 3-(2-bromophenyl)-2-(4-methylphenyl)-3-oxopropanal 
• 220503-15-1 C₁₅H₁₃BrO 

Downstream Products

• 42327-60-6 4’-methylisoflavanone 
• 1606136-83-7 2-methyl-6-(4-methylphenyl)-7-(2-hydroxylphenyl)pyrazolo[1,5-a]pyrimidine 
• 1456626-69-9 3-cyano-6-(2-hydroxyphenyl)-5-(4-methylphenyl)pyridin-2(1H)-one 
• 1427272-76-1 3-cyano-6-(2-hydroxylphenyl)-5-(4-methylphenyl)pyridine-2-(1H)-thione 

Relevant articles and documents

Novel Synthesis of Isoflavones by the Palladium-Catalyzed Cross-Coupling Reaction of 3-Bromochromones with Arylboronic Acids or Its Esters

The synthesis of isoflavone derivatives by means of palladium-catalyzed cross-coupling reaction between 3-bromochromones and arylboronic acids or its butyl esters is described.

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.

Scaffold-hopping of bioactive flavonoids: Discovery of aryl-pyridopyrimidinones as potent anticancer agents that inhibit catalytic role of topoisomerase IIα

A strategy of scaffold-hopping of bioactive natural products, flavones and isoflavones, leading to target-based discovery of potent anticancer agents has been reported for the first time. Scaffold-hopped flavones, 2-aryl-4H-pyrido[1,2-a]pyrimidin-4-ones and the scaffold-hopped isoflavones, 3-aryl-pyrido[1,2-a]pyrimidin-4-ones were synthesized via Pd-catalyzed activation–arylation methods. Most of the compounds were found to exhibit pronounced human topoisomerase IIα (hTopoIIα) inhibitory activities and several compounds were found to be more potent than etoposide (a hTopoIIα-inhibiting anticancer drug). These classes of compounds were found to be hTopoIIα-selective catalytic inhibitors while not interfering with topoisomerase I and interacted with DNA plausibly in groove domain. Cytotoxicities against various cancer cells, low toxicity in normal cells, and apoptotic effects were observed. Interestingly, compared to parent flavones/isoflavones, their scaffold-hopped analogs bearing alike functionalities showed significant/enhanced hTopoIIα-inhibitory and cytotoxic properties, indicating the importance of a natural product-based scaffold-hopping strategy in the drug discovery.