1486-63-1

Upstream product

• 117-39-5 quercetol 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 1064-06-8 3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one 
• 13157-90-9 2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)chromen-4-one 
• 13459-13-7 7,4’-di-O-benzylquercetin 

Downstream Products

• 1592-68-3 2-(3,4-bis(benzyloxy)phenyl)-3,7-(dibenzyloxy)-5-methoxy-4H-chromen-4-one 
• 357194-05-9 3,7-dihydroxy-2-(3,4-dihydroxyphenyl)-5-(β-D-galactopyranosyloxy)-4H-1-benzopyran-4-one 
• 357194-16-2 3,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]-5-(β-D-galactopyranosyloxy)-4H-1-benzopyran-4-one 
• 529-51-1 5-O-methylquercetin 
• 1610737-76-2 2-(3,4-dihydroxyphenyl)-5-((4-fluorobenzyl)oxy)-3,7-dihydroxy-4H-chromen-4-one 
• 1610737-58-0 3,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-5-((4-fluorobenzyl)oxy)-4H-chromen-4-one 
• 1355333-76-4 3,7-di(benzyloxy)-2-(3,4-dibenzyloxyphenyl)-5-allyloxy-4-oxo-4H-chromene 
• 1355333-54-8 3,7-(dihydroxy)-2-(3,4-dihydroxyphenyl)-5-propyloxy-4-oxo-4H-chromene 
• 1313191-76-2 3,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-5-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-4H-chromen-4-one 
• 34199-21-8 quercetin 5‐O‐β‐D‐glucopyranoside 
• 40554-90-3 3,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-5-β-D-glucopyranosyloxy-4H-chromen-4-one 
• 367522-85-8 quercetin 5-O-β-D-glucuronide 
• 1144104-67-5 Methyl 2-((3,7-Bis(benzyloxy)-2-(3,4-bis(benzyloxy)-phenyl)-4-oxo-4H-chromen-5-yl)oxy)acetate 

Relevant academic research and scientific papers

Clarification of the role of quercetin hydroxyl groups in superoxide generation and cell apoptosis by chemical modification

Accumulated data have suggested that the hydroxyl groups of flavonoids are important for their bioactive function. To directly demonstrate the role of hydroxyl groups, we synthesized a derivative of quercetin, 3,7,3',4'-0- tetrabenzylquercetin (4Bn-Q) tha

Flavonoid-based inhibitors of the Phi-class glutathione transferase from black-grass to combat multiple herbicide resistance

The evolution and growth of multiple-herbicide resistance (MHR) in grass weeds continues to threaten global cereal production. While various processes can contribute to resistance, earlier work has identified the phi class glutathione-S-transferase (AmGSTF1) as a functional biomarker of MHR in black-grass (Alopecurus myosuroides). This study provides further insights into the role of AmGSTF1 in MHR using a combination of chemical and structural biology. Crystal structures of wild-type AmGSTF1, together with two specifically designed variants that allowed the co-crystal structure determination with glutathione and a glutathione adduct of the AmGSTF1 inhibitor 4-chloro-7-nitro-benzofurazan (NBD-Cl) were obtained. These studies demonstrated that the inhibitory activity of NBD-Cl was associated with the occlusion of the active site and the impediment of substrate binding. A search for other selective inhibitors of AmGSTF1, using ligand-fishing experiments, identified a number of flavonoids as potential ligands. Subsequent experiments using black-grass extracts discovered a specific flavonoid as a natural ligand of the recombinant enzyme. A series of related synthetic flavonoids was prepared and their binding to AmGSTF1 was investigated showing a high affinity for derivatives bearing a O-5-decyl-α-carboxylate. Molecular modelling based on high-resolution crystal structures allowed a binding pose to be defined which explained flavonoid binding specificity. Crucially, high binding affinity was linked to a reversal of the herbicide resistance phenotype in MHR black-grass. Collectively, these results present a nature-inspired new lead for the development of herbicide synergists to counteract MHR in weeds. This journal is

Quercetin derivative and preparation method thereof (by machine translation)

The invention discloses a quercetin derivative and a preparation method, and application thereof. The invention belongs to the field, and aims to solve the problems, such as poor water solubility, low bioavailability and the like in the prior art, provides a quercetin derivative, and the obtained quercetin derivative is far better than quercetin, has higher bioavailability, and can be used for treating cardiovascular and cerebrovascular diseases, resisting cancers and preventing cancer. Another object of the present invention is to provide a method, using quercetin, for protecting a hydroxyl, followed by substitution reaction and hydrogenation reaction to prepare a quercetin derivative, and a method for synthesizing the quercetin derivative. To the invention, the natural quercetin derivative, by substitution reaction at 5 - OH hydroxyl level, is beneficial to improving the water solubility and fat solubility, improving the bioavailability, and the method is simple in principle 37% - 57%, and high in product yield, 96% - 98%f =0000000.5. (by machine translation)

Natural and Synthetic Flavonoids as Potent Mycobacterium tuberculosis UGM Inhibitors

This study reports a novel class of inhibitors of uridine 5′-diphosphate (UDP) galactopyranose mutase (UGM) derived from a screening of natural products. This enzyme is an essential biocatalyst involved in the cell wall biosynthesis of Mycobacterium tuberculosis. Flavonoids are potent inhibitors of UGM. The synthesis of novel methylated flavonoids allowed a structure–activity relationship analysis to be performed and which functional groups and structural elements were required for UGM inhibition could be determined. The binding mode of one of the best inhibitors was found to be noncompetitive. Docking simulations indicated that this molecule was likely to bind UGM in its open conformation, in a cavity recently identified as a “druggable” pocket. Importantly, two of the best inhibitors of the M. tuberculosis UGM displayed moderate activity against whole M. tuberculosis cells. This study reports the first natural products that act as inhibitor of UGM. Given the importance of natural products in medicinal chemistry, these results create new opportunities for the discovery of new antitubercular agents.

Quercetin derivative and its preparation method and application

The invention discloses a quercetin derivative and a preparation method and application thereof. The preparation method comprises the following steps: firstly using dichlorodiphenylmethane to protect quercetin o-diphenol hydroxyl, combining a benzyl protection group to obtain the selectively protected quercetin derivative, and then independently reacting with dimethyl sulfate, diethyl sulfate, allyl bromide, paratoluensulfonyl chloride and acetic anhydride respectively to generate corresponding quercetin derivatives. All of the prepared derivative compounds have NRK-49F proliferation activity inhibition superior to that of quercetin. The quercetin derivatives 20a-1, 14a-1 and 23d-1 compositely replaced by methyl and p-tosyl have higher inhibition NRK-49F proliferation activity, and the inhibition ratio respectively reaches 86.33%, 78.04% and 75.91%. Thus, the currently obtained quercetin derivative compounds have obvious inhibition effect on kidney fibroblast NRK-49F proliferation.

Synthesis and characterization of novel flavonoid derivatives via sequential phosphorylation of quercetin

Flavonoids are naturally-occurring polyphenolics that have been implicated in a wide range of biological activities. The major obstacles to flavonoid applications are the poor solubility in common solvents. Phosphorylation of flavonoids yields a new class of flavonoid derivatives which are very soluble in aqueous solutions and hence have the potential to be used in biological studies. We hereby report the sequential phosphorylation of Quercetin leading to the synthesis of Quercetin pentaphosphate (QPP), Apigenin triphosphate (ATRP), 5,4′-Quercetin Diphosphate (5,4′-QDP) and 4′-Quercetin monophosphate (4′-QP) with solubility of 848?mg/mL, 367?mg/mL, 315?μg/mL and 106?μg/mL respectively. The synthesis of 4′-QP, 5,4′-QDP, QPP and ATRP was successful with 85%, 60.5%, 56% and 99% yield respectively. These compounds have been characterized using 1H NMR, 13C NMR, 31P NMR.

Effects of Functional Groups and Sugar Composition of Quercetin Derivatives on Their Radical Scavenging Properties

Quercetin derivatives are widespread in the plant kingdom and exhibit various biological actions. The aim of this study was to investigate the structure-activity relationships of quercetin derivatives, with a focus on the influence of functional groups and sugar composition on their antioxidant capacity. A series of quercetin derivatives were therefore prepared and assessed for their DPPH radical scavenging properties. Isoquercetin O-gallates were more potent radical scavengers than quercetin. The systematic analysis highlights the importance of the distribution of hydroxy substituents in isoquercetin O-gallates to their potency.

Design and discovery of flavonoid-based HIV-1 integrase inhibitors targeting both the active site and the interaction with LEDGF/p75

HIV integrase (IN) is an essential enzyme for the viral replication. Currently, three IN inhibitors have been approved for treating HIV-1 infection. All three drugs selectively inhibit the strand transfer reaction by chelating a divalent metal ion in the

Synthesis and identification of quercetin benzyl ethers

We have studied the effects of the benzylating agent character, the reactants ratio, and the solvent nature on the composition of the products of quercetin benzylation. The structure of the products has been confirmed by IR, UV, 1H NMR, 13

Regioselective iodination of flavonoids by N-iodosuccinimide under neutral conditions

Regioselective synthesis of C-6 and C-8 monoiodo flavonoids, which are important intermediates for the synthesis of flavonoid natural products and drug molecules, was achieved by iodination of suitably alkylated flavonoids with N-iodosuccinimide (NIS) in DMF. The iodination gives either a C-6 or C-8 iodo flavonoid in high yield, depending on the protection pattern of the C-5 and C-7 OH groups. The mild and neutral conditions render this novel protocol particularly useful for the regioselective iodination of acid-sensitive substrates.