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Usage

Chemical Properties

Yellow Solid

InChI:InChI=1/C36H30O5/c37-33(21-18-27-16-19-31(20-17-27)39-24-28-10-4-1-5-11-28)36-34(38)22-32(40-25-29-12-6-2-7-13-29)23-35(36)41-26-30-14-8-3-9-15-30/h1-23,38H,24-26H2/b21-18+

Upstream product

• 4397-53-9 p-benzyloxybenzaldehyde 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 18495-74-4 dibenzyl sulfate 
• 480-41-1 naringenin 
• 100-39-0 benzyl bromide 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 

Downstream Products

• 96333-59-4 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one 
• 527-95-7 herbacetin 
• 41440-05-5 isoscutellarein 
• 97828-25-6 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-8-iodo-4H-chromen-4-one 
• 101467-70-3 5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-4H-chromen-4-one 
• 849938-27-8 5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)-3-[3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyloxy]-4H-chromen-4-one 
• 896121-46-3 5,7-bis-benzyloxy-2-(4-benzyloxy-phenyl)-chroman-3-ol 
• 133882-73-2 Kaempferol-3-O-(2,4-di-O-acetyl-alpha-L-rhamnopyranoside) 
• 77307-50-7 Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside) 
• 135618-17-6 Kaempferol-3-O-(4-O-acetyl-alpha-L-rhamnopyranoside) 
• 482-39-3 kaempferol 3-rhamnoside 
• 916069-08-4 (2S,3S,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3- yl)oxy)-5-hydroxy-2-methyltetrahydro-2H-pyran-3,4-diyl diacetate 

Relevant academic research and scientific papers

Synthesis and Evaluation of the Acetylcholinesterase Inhibitory Activities of Some Flavonoids Derived from Naringenin

Alzheimer's disease (AD) is an irreversible neurodegenerative disease that affects many older people adversely. AD has been putting a huge socioeconomic burden on the healthcare systems of many developed countries with aging populations. The need for new therapies that can halt or reverse the progression of the disease is now extremely great. A research approach in the finding new treatment for AD that has attracted much interest from scientists for a long time is the reestablishment of cholinergic transmission through inhibition of acetylcholinesterase (AChE). Naringenin is a flavonoid with the potential inhibitory activity against AChE. From naringenin, many other flavonoid derivatives, such as flavanones and chalcones, can be synthesized. In this study, by applying the Williamson method, nine flavonoid derivatives were synthesized, including four flavanones and five chalcones. The evaluation of AChE inhibitory activity by the Ellman method showed that there were four substances (2, 4, 5, and 7) with relatively good biological activities (IC50 100 μM), and these biological activities were better than that of naringenin. The molecular docking revealed that strong interactions with amino acid residue Ser200 of the catalytic triad and those of the peripheral region of the enzyme were crucial for strong effects against AChE. Compound 7 had the strongest AChE inhibitory activity (IC50 13.0 ± 1.9 μM). This substance could be used for further studies.

Facile synthesis of norwogonin, isoscutellarein, and herbacetin

An expeditious synthesis of norwogonin, isoscutellarein, and herbacetin, has been accomplished by a strategy featuring a borylation of sterically hindered aryl iodide and a one-pot oxidation to generate the C-3 and C-8 OH groups. The total synthesis gives excellent yields and conventional flash column chromatography is not needed for purification.

De novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation

(Chemical Equation Presented) The enantioselective syntheses of naturally occurring kaempferol glycoside SL0101 (1a) and its analogues 1b-e, as well as their enantiomers, have been achieved in 7-10 steps. The routes rely upon a diastereoselective palladium-catalyzed glycosylation, ketone reduction, and dihydroxylation to introduce the rhamno-stereochemistry. The asymmetry of the sugar moiety of these kaempferol glycosides was derived from Noyori reduction of an acylfuran. An acetyl group shift from an axial (C-2) to equatorial position (C-3) under basic conditions was also described.

Synthesis of a potent and selective inhibitor of p90 Rsk

(Chemical Equation Presented) The synthesis of the naturally occurring kaempferol glycoside SL0101 has been accomplished, as has its biochemical evaluation. SL0101 exhibits selective and potent p90 Rsk inhibitory activity at nanomolar concentrations without inhibiting the function of upstream kinases such as MEK, Raf, or PKC. The synthesis verified the structural assignment of the natural product and has provided access to material sufficient for detailed biological evaluation.

Synthesis of (±)-lotthanongine, a novel natural product with a flavan-indole hybrid structure

First total synthesis of lotthanongine (3), a natural product with a flavan-indole composite structure, has been achieved via the Lewis acid-catalyzed C-C bond formation between the catechin and the indole units.

A structure-activity study for the inhibition of metalloproteinase-9 activity and gene expression by analogues of gallocatechin-3-gallate

Catechins are able to modulate the gelatinolytic activity of matrix metalloproteinase-9 (MMP-9) by reducing its release from macrophages. Gallocatechins decrease MMP-9 secretion by lowering MMP-9 promoter activity and mRNA levels. The effect appears to be dependent on some structural and stereochemical requirements. In this study, the relationship between chemical structure and activity was studied by testing the effect of analogues of (±)-gallocatechin-3-gallate (±)-GCG, selectively deprived of hydroxyl groups, on MMP-9 activity, transcription, and secretion. Our results indicate that (±)-GCG and (±)-catechin-3-gallate are characterized by a substitution pattern compatible with direct inhibition of MMP-9 activity. Conversely, when transcription was the target, (±)-trans-3-flavanol-3- benzoate, lacking all the hydroxyl groups, was the most effective both in lowering MMP-9 promoter activity and consequently protein secretion, and in inhibiting nuclear-factor-κB-driven transcription. Our results suggest that the structural requirements for enzyme inhibition are different from those necessary for targeting gene expression. Birkhaeuser Verlag, 2005.

Practical synthesis of a C-glycosyl flavonoid via O→C glycoside rearrangement

The C-glycosylation of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride and 2-acetylphloroglucinol 3,5-bis(alkyl ether) in the presence of boron trifluoride etherate as an activator stereoselectively gave the β-C-glucoside in a good yield via O→C glycos

Syntheses of Several Dihydrochalcone-Amino Acid and -Peptide Conjugates

In order to find out some specific blockers of the membrane transport of amino acids and small peptides in animal small intestine and kidney, the following dihydrochalcone (DHC)-amino acid and -peptide conjugates were synthesized. acetylglycyl>glycine.Nε-acetyllysine, O-homoserine, homoseryl>glycine, N-glycyl-O-homoserine, and homoseryl>glycine.

Synthesis of natural 5,7-dihydroxy-3-(4-hydroxybenzyl)chromone and its congener

2-Hydroxy-4,6-dibenzyloxyacetophenone (1) on condensation with p-benzyloxybenzaldehyde (2a) or veratraldehyde (2b) gives the corresponding chalcone (3a or 3b) which is reduced to dihydrochalcone (4a or 4b).The latter undergoes cyclization with DMF in the presence of borontrifluoride etherate and methanesulphonyl chloride to give 5,7-dihydroxy-3-(4-hydroxybenzyl)chromone (5a), identical with naturally occuring compound, or 5,7-dihydroxy-3-(3,4-dimethoxybenzyl)chromone (5b).