89839-87-2

Basic information

• Product Name: 2-(4-methylphenyl)-2,3-dihydro-4H-chromen-4-one
• CAS NO: 89839-87-2
• Molecular Weight: 238.286
• Mol File: 89839-87-2.mol
• Article Data: 46

Chemical Properties

• CAS DataBase Reference: 2-(4-methylphenyl)-2,3-dihydro-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-methylphenyl)-2,3-dihydro-4H-chromen-4-one(89839-87-2)
• EPA Substance Registry System: 2-(4-methylphenyl)-2,3-dihydro-4H-chromen-4-one(89839-87-2)

Safety Data

• Hazardous Substances Data: 89839-87-2(Hazardous Substances Data)

Upstream product

• 132589-36-7 1-(4-methylphenyl)prop-2-yn-1-ol 
• 108-95-2 phenol 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 5720-05-8 4-methylphenylboronic acid 
• 3055-86-5 3-phenoxypropionitrile 
• 90-02-8 salicylaldehyde 
• 766-97-2 4-n-methylphenylacetylene 
• 533-58-4 2-Iodophenol 
• 104-87-0 4-methyl-benzaldehyde 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 491-38-3 1-benzopyran-4(4H)-one 
• 7645-95-6 2-hydroxy-4'-methyl-chalcone 
• 118-93-4 o-hydroxyacetophenone 
• 24431-15-0 N-benzyl-p-tolylmethanimine 

Downstream Products

• 1372550-17-8 1-[(4-chloro-2-(p-tolyl)-2H-chromen-3-yl)-methylene]-2-phenylhydrazine 
• 1370351-83-9 1-phenyl-4-(4-methylphenyl)-1,4-dihydrochromeno[4,3-c]pyrazole 
• 1370351-84-0 1-(4-chlorophenyl)-4-(p-tolyl)-1,4-dihydrochromeno[4,3-c]pyrazole 
• 80907-22-8 ethyl 2?(4?oxo?2?p?tolyl?4H?chromen?3?yl)acetate 
• 19275-68-4 3-Hydroxy-4'-methylflavone 
• 1393598-16-7 5-(4-methylphenyl)-2-piperidino-5H-chromeno[3,4-c]pyridine-1-carbonitrile 
• 534569-38-5 C₁₇H₁₇N₃O₂ 
• 373357-13-2 4-chloro-2-(4-methyl phenyl)-2H-3-chromene carbaldehyde 
• 89839-88-3 (+/-)-cis-4'-methylflavan-4-ol 
• 34000-27-6 (2E)-1-(2-hydroxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one 
• 58113-12-5 3-(4-methylphenyl)-4H-chromen-4-one 
• 41255-30-5 4'-methylflavone 

Relevant articles and documents

PHOTO-OXIDATIVE CYCLISATION OF 2'-HYDROXYCHALCONES LEADING TO FLAVONES INDUCED BY HETEROCYCLE N-OXIDES: HIGH EFFICIENCY OF PYRIMIDOPTERIDINE N-OXIDE FOR THE PHOTOCHEMICAL DEHYDROGENATION

Irradiation of 2'-hydroxychalcones (3) with UV-visible light in the presence of heterocycle N-oxides such as pyrimidopteridine N-oxide (I) results in the formation of the corresponding flavones (4) and flavanones (5).The photooxidative cyclisation of (3) induced by (1) to give (4) most efficiently occurred among the heterocycle N-oxides examined and could be reasonably explained by considering an initial single-electron oxidation of (3) by (1) under the photochemical conditions and subsequent intramolecular cyclisation.

Synthesis and kinetic study for the interconversion process of some 2'-hydroxychalcones to their corresponding flavanones

In this work, five substituted2'-Hydroxychalconeswere prepared using Claisen - Schmidt condensation and used as a synthone for substituted flavanones via base catalyzed isomerization process. The latter process has been studied kinetically using HPLC technique in (8:2) (CH3CN:CH3OH) medium at different temperatures (298 K - 318 K). The obtained results were inconsonance with a four-step mechanism which considered the existence of phenoxide ion as the key intermediate. The reaction was achieved as a pseudo first order reaction in which the rate of the studied compounds followed the sequence 1>2>3>4>5, and the activation energy had the same sequence for these compounds. The reaction rate was affected by the electronic behavior of the different substituents at ring B since they played an important role in the stability of the intermediate that led to the final product.

Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis

Peptidyl-prolyl cis-trans isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (AF-39) was identified as a novel Pin1 inhibitor. Biochemical tests indicate that AF-39 potently inhibits Pin1 activity with an IC50 values of 1.008 μm, and also displays high selectivity for Pin1 among peptidyl prolyl isomerases. Furthermore, AF-39 significantly suppresses cell proliferation of HCC cells in a dose- and time-dependent manner. Mechanistically, AF-39 regulates the subcellular distribution of XPO5 and increases miRNAs biogenesis in HCC cells. This work provides a promising lead compound for HCC treatment, highlighting the therapeutic potential of miRNA-based therapy against human cancer.