23671-72-9Relevant academic research and scientific papers
Ecofriendly synthesis of halogenated flavonoids and evaluation of their antifungal activity
Bernini, Roberta,Pasqualetti, Marcella,Provenzano, Gianfranco,Tempesta, Sabrina
, p. 2980 - 2987 (2015/04/22)
Brominated and chlorinated flavonoids belonging to different classes (flavanones, flavones and catechins) were prepared from the corresponding flavonoids by a simple and ecofriendly procedure based on the use of sodium halides, aqueous hydrogen peroxide and acetic acid. Pure samples of substrates and products were tested against Trichoderma koningii, Fusarium oxysporum and Cladosporium cladosporioides, common saprotrophic soil and seed fungi, potential pathogens for humans and their activity was expressed as linear mycelial growth inhibition (%). Among them, 8-chloro-5,7,3′,4′-tetramethoxyepicatechin 29, a novel catechin derivative, exhibited a remarkable effect against all tested fungi also at low concentrations.
Studies in polyphenol chemistry and bioactivity. 3. Stereocontrolled synthesis of epicatechin-4α,8-epicatechin, an unnatural isomer of the B-type procyanidins
Kozikowski,Tueckmantel,Hu
, p. 1287 - 1296 (2007/10/03)
Oligomeric procyanidins containing 4α-linked epicatechin units are rare in nature and have hitherto not been accessible through stereoselective synthesis. We report herein the preparation of the prototypical dimer, epicatechin-4α,8-epicatechin (6), by reaction of the protected 4-ketones 11a,b with aryllithium reagents derived by halogen/metal exchange from the awl bromides 26a,b. Removal of the 4-hydroxyl group from the resulting tertiary benzylic alcohols 27a,b was effected by tri-n-butyltin hydride and trifluoroacetic acid in a completely stereoselective manner, resulting in hydride delivery exclusively from the β face. If benzyl was chosen for protection of the 3-hydroxyls, all protective groups could subsequently be removed in a single step by hydrogenolysis, tert-Butyldimethylsilyl groups, on the other hand, permitted selective deprotection of the 3-hydroxyls in preparation for their subsequent acylation with tri-O-benzylgalloyl chloride. Only monogalloylation at the "bottom" 3-hydroxyl took place when 28c was acylated under the previously reported conditions, reflecting the increased steric hindrance of the "top" 3-hydroxyl group in 28c compared with its 4β,8-isomer 3. The preparation of compounds 14 and 17 containing phloroglucinol trimethyl ether in the 4α and 4β linkages to epicatechin is also described. The 8-position of the bromine atom in 19, previously conjectured in analogy to the structurally characterized tetramethyl ether 20, was confirmed by transformation of both compounds into the common derivative 25.
Synthesis of Condensed Tannins. Part 12. Direct Access to - and -all-2,3-cis-Procyanidin Derivatives from (-)-Epicatechin: Assessment of Bonding Positions in Oligomeric Analogues from Crataegus oxyacantha L.
Kolodziej, Herbert,Ferreira, Daneel,Roux, David G.
, p. 343 - 350 (2007/10/02)
Synthesis of methyl ester acetates of - and -all-2,3-cis-procyanidin biflavanoids is effected by oxidative functionalization of (-)-epicatechin tetramethyl ester with lead tetra-acetate, and condensation of the resultant 2,3-cis-flavan-3,4-diol
Electrophilic Aromatic Substitution of Catechins: Bromination and Benzylation
McGraw, Gerald W.,Hemingway, Richard W.
, p. 973 - 978 (2007/10/02)
Relative yields of C-6, C-8, and C-6 and C-8 substituted catechins obtained from the reaction of (+)-catechin or 3',4',5,7-tetra-O-methyl-(+)-catechin with pyridinium hydrobromide-perbromide, bromine, p-hydroxybenzyl alcohol, or o-hydroxybenzyl alcohol sh
Synthesis of Condensed Tannins. Part 3. Chemical Shifts for Determining the 6- and 8-Bonding Positions of 'Terminal' (+)-Catechin Units
Hundt, Hans K. L.,Roux, David G.
, p. 1227 - 1234 (2007/10/02)
Pairs of 6- and 8-functionalised (Br, OH, OAc, CO2Me, and CH2Me groups) 3',4',5,7-tetra-O-methyl-(+)-catechins available through selective bromination and debromination reactions and hence via lithio-analogues, provide diagnostic chemical shifts of their
