1222-12-4

Basic information

• Product Name: 6-bromo-3-hydroxy-2-phenyl-4H-chromen-4-one
• Synonyms: 6-bromo-3-hydroxy-2-phenyl-4H-chromen-4-one
• CAS NO: 1222-12-4
• Molecular Weight: 317.139
• Mol File: 1222-12-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 6-bromo-3-hydroxy-2-phenyl-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromo-3-hydroxy-2-phenyl-4H-chromen-4-one(1222-12-4)
• EPA Substance Registry System: 6-bromo-3-hydroxy-2-phenyl-4H-chromen-4-one(1222-12-4)

Safety Data

• Hazardous Substances Data: 1222-12-4(Hazardous Substances Data)

Upstream product

• 1220531-63-4 6-bromo-2-phenylchroman-4-one 
• 1218-22-0 (E)-1-(5-bromo-2-hydroxyphenyl)-3-phenylprop-2-en-1-one 
• 1218-22-0 3-phenyl-1-(2'-hydroxy-5'-bromophenyl)-2-propen-1-one 
• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 100-52-7 benzaldehyde 

Downstream Products

• 1446340-56-2 C₂₉H₂₂O₂ 
• 1446340-57-3 C₂₇H₁₆Cl₂O₂ 
• 1446340-58-4 C₂₇H₁₆F₂O₂ 
• 1446340-60-8 6-bromo-3-(4-methoxyphenyl)-2-phenyl-4H-chromen-4-one 
• 1446340-61-9 C₂₃H₁₇BrO₃ 
• 1446340-62-0 C₂₂H₁₅BrO₃ 
• 1446340-63-1 C₂₁H₁₂BrClO₂ 
• 1446340-64-2 C₂₁H₁₂BrFO₂ 
• 1446340-65-3 C₂₁H₁₂BrFO₂ 
• 1446340-66-4 C₂₂H₁₂BrF₃O₂ 
• 1446340-67-5 C₂₉H₂₁FO₃ 
• 1446340-68-6 C₂₉H₂₁FO₃ 
• 1446340-69-7 C₃₀H₂₄O₃ 
• 1446340-70-0 C₂₇H₁₆ClFO₂ 

Relevant articles and documents

Synthesis of Flavonols via Pyrrolidine Catalysis: Origins of the Selectivity for Flavonol versus Aurone

A novel synthetic method for flavonol from 2′-hydroxyl acetophenone and benzaldehyde promoted by pyrrolidine under an aerobic condition in water is established. This protocol was supported by efficient synthesis of 44 common examples and three natural products. The α, β-unsaturated iminium ion (enimine ion E) was proved to be the key intermediate in the reaction. H218O and 18O2 isotope tracking experiments demonstrated that both water and the aerobic atmosphere were necessary to ensure the transformation. The selectivity for flavonol or aurone was originated from solvent-triggered intermediates, which were determined by UV-visible spectra from isolated enimine. The phenol-iminium E-A is dominant in water and the ketoenamine intermediate E-B is prevalent in acetonitrile. In the presence of pyrrolidine and oxygen, E-A leads to flavonol through E-I, a zwitterionic-like phenoloxyl-iminium ion, following the key steps of cyclization and a [2 + 2] oxidation; E-B proceeds through path II, a radical process induced by photolysis of E-B with both pyrrolidine and oxygen, to afford aurone. Preliminary mechanistic studies are reported.

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.

Chemoselective Suzuki-Miyaura cross-coupling reactions of 6-bromo-3-(trifluoromethylsulfonyloxy)flavone

Arylated flavones were prepared by Suzuki-Miyaura reactions of 6-bromo-3-(trifluoro-sulfonyloxy)flavone. The reactions proceeded with very good chemoselectivity in favor of position 3. Georg Thieme Verlag Stuttgart · New York.