87292-54-4

Basic information

• Product Name: 2H-1-Benzopyran-3(4H)-one, 2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-, (2R)-
• CAS NO: 87292-54-4
• Molecular Formula: C43H36O6
• Molecular Weight: 648.755
• Mol File: 87292-54-4.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 2H-1-Benzopyran-3(4H)-one, 2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-, (2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-3(4H)-one, 2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-, (2R)-(87292-54-4)
• EPA Substance Registry System: 2H-1-Benzopyran-3(4H)-one, 2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-, (2R)-(87292-54-4)

Safety Data

• Hazardous Substances Data: 87292-54-4(Hazardous Substances Data)

Upstream product

• 301539-02-6 3,5,7,3',4'-penta-O-benzylepicatechin 
• 154-23-4 catechin 
• 100-39-0 benzyl bromide 
• 253336-68-4 3,4-bis(phenylmethoxy)-benzonitrile 
• 918158-03-9 (1S,2S)-3-[2,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-(3,4-bis-benzyloxy-phenyl)-propane-1,2-diol 
• 918157-97-8 (E)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4-bis(benzyloxy)phenyl]propene 
• 732298-11-2 (+)-(1S,2S)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-[3,4-bis(benzyloxy)phenyl]propane-1,2-diol 
• 732298-08-7 (E)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-[3,4-bis(benzyloxy)phenyl]propene 
• 362632-29-9 (E)-3-(3,4-bis(benzyloxy)phenyl)prop-2-en-1-ol 
• 203571-40-8 3-(3,4-bis-benzyloxy-phenyl)-acrylic acid ethyl ester 
• 63604-98-8 1,3-dibenzylphloroglucinol 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 

Downstream Products

• 664351-39-7 (2R,3R,4S)-5,7,3',4'-tetrabenzyloxy-4-(2''-ethoxyethoxy)flavan-3-ol 
• 1282609-52-2 C₂₅H₂₄O₁₁ 
• 1018677-68-3 5,7,3',4'-tetra-O-benzyl-3-(3'',4'',5''-trimethoxybenzoyl)-(-)-epicatechin 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 87292-49-7 5,7,3',4'-tetra-O-benzylepicatechin 
• 1608504-14-8 C₅₆H₆₂O₈Si 
• 1608504-44-4 C₅₀H₄₇FO₇ 
• 1608504-43-3 C₅₀H₄₇FO₇ 
• 1608504-33-1 C₅₀H₄₈O₈ 
• 1608504-32-0 C₅₀H₄₈O₈ 
• 1608504-22-8 C₁₉H₁₈O₇ 

Relevant articles and documents

Asymmetric total synthesis of talienbisflavan A

The first asymmetric total syntheses of talienbisflavan A and bis-8,8′-epicatechinylmethane as well as a facile synthesis of bis-8,8′-catechinylmethane has been accomplished from readily available starting materials by using a newly developed direct regio

Towards the discovery of drug-like epigallocatechin gallate analogs as Hsp90 inhibitors

(-)-Epigallocatechin gallate (EGCG) is the major flavonoid of green tea and has been widely explored for a range of biological activities including anti-infective, anti-inflammatory, anti-cancer, and neuroprotection. Existing structure-activity data for EGCG has been largely limited to exploration of simple ethers and hydroxyl deletion. EGCG has poor drug-like properties because of multiple phenolic hydroxyl moieties and a metabolically labile ester. This work reports a substantial expansion of structure-activity understanding by exploring a range of semi-synthetic and synthetic derivatives with ester replacements and variously substituted aromatic and alicyclic groups containing more drug-like substituents. Structure-activity relationships for these molecules were obtained for Hsp90 inhibition. The results indicate that amide and sulfonamide linkers are suitable ester replacements. Hydroxylated aromatic rings and the cis-stereochemistry in EGCG are not essential for Hsp90 inhibition. Selected analogs in this series are more potent than EGCG in a luciferase refolding assay for Hsp90 activity.

Factors influencing the antifolate activity of synthetic tea-derived catechins

Novel tea catechin derivatives have been synthesized, and a structure-activity study, related to the capacity of these and other polyphenols to bind dihydrofolate reductase (DHFR), has been performed. The data showed an effective binding between all molecules and the free enzyme, and the dissociation constants of the synthetic compounds and of the natural analogues were on the same order. Polyphenols with a catechin configuration were better DHFR inhibitors than those with an epicatechin configuration. Antiproliferative activity was also studied in cultured tumour cells, and the data showed that the activity of the novel derivatives was higher in catechin isomers. Derivatives with a hydroxyl group para on the ester-bonded gallate moiety presented a high in vitro binding to DHFR, but exhibited transport problems in cell culture due to ionization at physiologic pHs. The impact of the binding of catechins to serum albumin on their biological activity was also evaluated. The information provided in this study could be important for the design of novel medicinal active compounds derived from tea catechins. The data suggest that changes in their structure to avoid serum albumin interactions and to facilitate plasmatic membrane transport are essential for the intracellular functions of catechins.