1632119-73-3

Basic information

• Product Name: 3-(4-HYDROXYPHENYL)-1-(2,4,6-TRIMETHOXYPHENYL)-2-PROPEN-1-ONE
• Synonyms: 3-(4-HYDROXYPHENYL)-1-(2,4,6-TRIMETHOXYPHENYL)-2-PROPEN-1-ONE;4-HYDROXY-2',4',6'-TRIMETHOXYCHALCONE
• CAS NO: 1632119-73-3
• Molecular Formula: C18H18O5
• Molecular Weight: 314.33
• Mol File: 1632119-73-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(4-HYDROXYPHENYL)-1-(2,4,6-TRIMETHOXYPHENYL)-2-PROPEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-HYDROXYPHENYL)-1-(2,4,6-TRIMETHOXYPHENYL)-2-PROPEN-1-ONE(1632119-73-3)
• EPA Substance Registry System: 3-(4-HYDROXYPHENYL)-1-(2,4,6-TRIMETHOXYPHENYL)-2-PROPEN-1-ONE(1632119-73-3)

Safety Data

• Hazardous Substances Data: 1632119-73-3(Hazardous Substances Data)

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 99-93-4 4-Hydroxyacetophenone 

Relevant articles and documents

Analogues of xanthones——Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates

Two series of compounds (chalcones and bis-chalcones) were designed, synthesized, and evaluated as α-glucosidase inhibitors (AGIs) with 1-deoxynojirimycin as positive control in vitro. Most of the compounds with two or four hydroxyl groups showed better inhibitory activities than 1-deoxynojirimycin towards α-glucosidase with noncompetitive mechanism. Moreover, most of the hydroxy bis-chalcones exhibit good α-glucosidase inhibitory activities in enzyme test. Inspiringly, bis-chalcones 2g (at 1 μM concentration) has stronger effect than 1-deoxynojirimycin on reducing the glucose level in HepG-2 cells (human liver cancer cell line).

Synthesis of xanthohumol analogues and discovery of potent thioredoxin reductase inhibitor as potential anticancer agent

The selenoprotein thioredoxin reductases (TrxRs) are attractive targets for anticancer drugs development. Xanthohumol (Xn), a naturally occurring polyphenol chalcone from hops, has received increasing attention because of its multiple pharmacological activities. We synthesized Xn and its 43 analogues and discovered that compound 13n displayed the highest cytotoxicity toward HeLa cells (IC50 = 1.4 μM). Structure-activity relationship study indicates that the prenyl group is not necessary for cytotoxicity, and introducing electron-withdrawing group, especially on the meta-position, is favored. In addition, methylation of the phenoxyl groups generally improves the potency. Mechanistic study revealed that 13n selectively inhibits TrxR and induces reactive oxygen species and apoptosis in HeLa cells. Cells overexpressing TrxR are resistant to 13n insult, while knockdown of TrxR sensitizes cells to 13n treatment, highlighting the physiological significance of targeting TrxR by 13n. The clarification of the structural determinants for the potency would guide the design of novel potent molecules for future development.