183067-65-4

Upstream product

• 100-44-7 benzyl chloride 
• 153-18-4 rutin 
• 100-39-0 benzyl bromide 
• 117-39-5 quercetol 

Downstream Products

• 879217-58-0 methanesulfonic acid 7-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-5-hydroxy-4-oxo-4H-chromen-3-yl ester 
• 1309453-97-1 C₆₂H₅₄O₁₆ 
• 1309453-94-8 C₅₆H₄₈O₁₃ 
• 1309453-96-0 C₅₅H₄₈O₁₆ 
• 1486-70-0 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on 
• 1486-57-3 2-(3,4-bis(benzyloxy)phenyl)-7-(benzyloxy)-5-hydroxy-3-methoxy-4H-chromen-4-one 
• 1486-56-2 2-(3,4-bis(benzyloxy)phenyl)-7-(benzyloxy)-3,5-dimethoxy-4H-chromen-4-one 
• 1469894-73-2 7-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-5-hydroxy-4-oxo-4H-chromen-3-yl 7-(2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-ylamino)-2-oxoethylamino)-7-oxoheptanoate 
• 1469894-74-3 7-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-5-hydroxy-4-oxo-4H-chromen-3-yl 7-(2-(4-hydroxyphenylamino)-2-oxoethylamino)-7-oxoheptanoate 

Relevant academic research and scientific papers

Synthesis of montbretin A analogues yields potent competitive inhibitors of human pancreatic α-amylase

Simplified analogues of the potent human amylase inhibitor montbretin A were synthesised and shown to bind tightly, KI = 60 and 70 nM, with improved specificity over medically relevant glycosidases, making them promising candidates for controlling blood glucose. Crystallographic analysis confirmed similar binding modes and identified new active site interactions.

Preparation of quercetin combined hydrogen sulfide donor and application of quercetin combined hydrogen sulfide donor in treatment of diabetes and wound healing of diabetes

The invention belongs to the technical field of preparation of medicines for treating diabetes and healing wounds of the diabetes, and particularly relates to quercetin-3-O-acetic acid-(4-(3H-1,2-dithiole-3-thioketone))-phenyl ester and an application thereof in preparation of medicines for treating diabetes and healing wounds of the diabetes. The preparation comprises the steps: by taking rutin as a raw material, carrying out substitution hydrolysis reaction twice, reducing to generate quercetin-3-O-acetic acid, and carrying out condensation reaction on quercetin-3-O-acetic acid and a hydrogen sulfide donor 5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thioketone to successfully prepare a compound entity capable of simultaneously treating diabetes and promoting wound healing. In an HUVECs cell experiment, a cell proliferation experiment verifies that the HUVECs can be promoted to grow, and a scratch experiment and an in-vitro tubule formation experiment further verify that the HUVECs can be promoted to heal wounds of diabetic patients. HepG 2 cytotoxicity experiments prove that the medicine has no damage to liver cells, and through treatment of an insulin resistance model, it is verified that the compound has a similar hypoglycemic effect with a commercially available medicine metformin.

Synthesis, characterization and antioxidant activity of quercetin derivatives

A series of quercetin derivatives were synthesized via Williamson etherification, Steglich esterification or Koenigs–Knorr glycosylation reaction at 3 and 7 position hydroxyl groups selectively. The structures of the synthesized compounds were characteriz

Extensive structure modification on luteolin-cinnamic acid conjugates leading to BACE1 inhibitors with optimal pharmacological properties

BACE1 inhibitory conjugates derived from two natural products, luteolin (1) and p-hydroxy-cinnamic acid (2), were subjected to systematic structure modifications, including various positions in luteolin segment for conjugation, different linkers (length, bond variation), as well as various substitutions in cinnamic acid segment (various substituents on benzene, and replacement of benzene by heteroaromatics and cycloalkane). Optimal conjugates such as 7c and 7k were chosen on the basis of a series of bioassay data for further investigation.

The first synthesis of 3-O-methylcyanidin and the effect of 3-O-substitution on stability under acidic conditions

The simplest and most common anthocyanin in nature is 3-O-glucosylcyanidin (1), and 3-O-glucosylation is believed to stabilize the chromophore. To clarify the effect of the glucose residue we compared the stability of 1 with its aglycone, cyanidin (2), an

Regiospecific synthesis of three quercetin O-β-glucosides of N-acetylglucosamine

The regiospecific synthesis of three quercetin O-β-glucosides of N-acetylglucosamine has been achieved in good yield. Selective di- and tri-O-benzylation of quercetin followed by O-glycosylation with 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl chloride under phase-transfer catalysis conditions yielded, after deacetylation and debenzylation, 3-, 3′- and 4′-glycosylated quercetin.

Quercetin derivative and preparation method and applications thereof

The invention discloses a quercetin derivative and a preparation method and applications thereof. The chemical structural formula of the quercetin derivative is represented by the formula (I). The chemical name of the quercetin derivative is 2-(3,4-dihydroxylphenyl)-3-(5-N,N-diethylaminepentyloxy)-5,7-dihydroxyl-4H-1-benzopyran-4-one. The 2-(3,4-dihydroxylphenyl)-3-(5-N,N-diethylaminepentyloxy)-5,7-dihydroxyl-4H-1-benzopyran-4-one is obtained by subjecting quercetin to chemical modification, can inhibit the activity of acetylcholin esterase, and can be used to prepare functional food or drugs for preventing Alzheimer's disease.

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.

Synthesis of quercetin-3-O-acetate and application of quercetin-3-O-acetate to tumor resistance

Quercetin has the pharmacological activities of eliminating phlegm, relieving cough, relieving asthma, lowering blood pressure, resisting cancer, resisting viruses, resisting bacteria, resisting oxidation and the like. The structure of quercetin is modified and transformed by utilizing a chemical method, so as to hopefully improve the bioavailability of quercetin and strengthen the pharmacological activities of quercetin. Quercetin selectively protected by benzyl bromide is utilized, and a Williamson reaction is utilized to introduce acetate to the third site of quercetin, so as to synthesize a series of quercetin-3-O-acetate derivants. An MTT method proves that compared with quercetin, the compound can obviously inhibit growth of esophagus cancer cells, and is a novel anti-tumor candidate compound with great potential.

Synthesis of quercetin glycosides and their α-glucosidase inhibitory activities

A series of quercetin glycosides as the analogues of 3,5,5'- Trimethyl-7-O-β-D-glucopyranosylquercetin (8) were synthesized, their structures were confirmed by 1H NMR, 13C NMR and MS. The inhibitory activities of those compounds against α-glucosidase were evaluated in vitro, in particular, the compounds V-c and V-d-2 showed promising bioactivities with IC50 of 19.4 μmol·L-1 and 19.7 μmol·L-1, are much higher than 8 (IC50 > 100 μmol·L-1). This research will provide a reference in the study of the synthetic methods and hypoglycemic activity for the quercetin glycosides.