55568-98-4

Upstream product

• 13328-96-6 cis-3-acetoxyflavan 
• 93514-42-2 2-phenylchromene 
• 20760-17-2 2-phenyl-3-oxo-3,4-dihydro-2H-1-benzopyran 
• 100-52-7 benzaldehyde 
• 888-12-0 (E)-2'-hydroxy-chalcone 
• 108-95-2 phenol 
• 138621-80-4 1-phenyl-1-phenoxy-2-propene 
• 121507-50-4 phenyl 1-phenyl-2-propynyl ether 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 24114-57-6 3-(2-hydroxyphenyl)-1-phenyl-1-propene 
• 1350895-98-5 C₁₇H₂₀O₄ 
• 1350895-97-4 C₁₇H₁₈O₂ 
• 1350895-99-6 (1R,2R)-3-(2-hydroxyphenyl)-1-phenylpropane-1,2-diol 
• 299412-43-4 3-O-(tert-butyldimethylsilyl)-5,7,3',4'-tetra-O-(trifluoromethanesulfonyl)epicatechin 

Relevant academic research and scientific papers

Catalytic Enantioselective Synthesis of 2-Aryl Chromenes and Related Phosphoramidite Ligands and Catalyst Compounds

Methods to access 2-aryl chromene compounds via an asymmetric catalytic process.

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.

Catalytic enantioselective synthesis of 2-aryl-chromenes

An enantioselective Pd-catalyzed 6-endo-trig reaction for the synthesis of 2-aryl-chromenes has been developed. A systematic optimization of a TADDOL-derived ligand set resulted in the identification of a novel monodentate phosphoramidite-palladium catalyst that accesses 2-aryl-2H-chromenes with high yield and enantioselectivity under mild conditions. The products obtained from this method can be transformed into biologically active compounds through functionalization of the chromene alkene. This journal is the Partner Organisations 2014.

Anti-staphylococcal activity and β-lactam resistance attenuating capacity of structural analogues of (-)-epicatechin gallate

We examined the impact of gradual removal of hydroxyl groups from the A- and B-rings of (-)-epicatechin gallate on antibacterial activity and oxacillin resistance attenuation of an epidemic strain of methicillin resistant Staphylococcus aureus. Removal of

Studies in polyphenol chemistry and bioactivity. 2. Establishment of interflavan linkage regio- and stereochemistry by oxidative degradation of an O-alkylated derivative of procyanidin B2 to (R)-(-)-2,4-diphenylbutyric acid

The assignment of interflavan bond regio- and stereochemistry in oligomeric proanthocyanidins has in the past relied on empirical spectroscopic techniques which are influenced by the conformation of the C rings. Only recently was the 4,8-regiochemistry of procyanidin B2 (3b) firmly established by 2-dimensional NMR methods. We describe herein the proof of 4β-stereochemistry in 3b by oxidative degradation of the derivative 3d bearing differential (O-benzyl and O-methyl) protecting groups in its 'top' and 'bottom' epicatechin moieties, to (R)-(-)-2,4-diphenylbutyric acid. The key elements of the degradative process are (1) removal of the C-3 alcohol functions through a modified Barton deoxygenation employing hypophosphorous acid as the reducing agent; (2) deprotection of the 'top' unit by hydrogenolysis, followed by exhaustive aryl triflate formation with N,N-bis-(trifluoromethanesulfonyl)aniline and DBU in DMF; (3) hydrogenolytic deoxygenation of the 'top' unit over Pearlman's catalyst with concomitant scission of the O-C2 bond; (4) selective oxidation of the 'bottom' unit with NaIO4/RuCl3. The hitherto unreported absolute configuration of (-)-2,4-diphenylbutyric acid was established as R by X-ray crystal structure analysis of the (R)-(+)-α-methylbenzylamine salt. As a corollary, the selectivity of hydrogenolytic and solvolytic reactions of epicatechin-derived tetrasulfonates has been investigated.

Reactions of Flav-2-enes and Flav-2-en-4-ones (Flavones)

Flav-2-enes, flavones, and 3-alkyl ethers of flavonols add alcohols and carboxylic acids in the presence of N-bromosuccinimide to give 2-alkoxy- and 2-acyloxy-3-bromoflavans which provide routes to cis-3-bromoflavans by reduction and to 3,4-diols by elimination and reaction with osmium tetraoxide.The 2-acyloxyflavans react with alcohols yielding 2-alkoxyflavans.Flavonols react with N-bromosuccinimide and alcohols to give bromine-free hemiacetals, the known 2,3-dialkoxy-3-hydroxyflavanones.