23423-35-0

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 77412-37-4 β,4-dihydroxy-2',4'-dimethoxydihydrochalcone 
• 77412-33-0 4-hydroxy-2',4'-dimethoxy-α-tosyloxydihydrochalcone 
• 74189-56-3 4-(tetrahydropyran-2-yloxy)benzaldehyde 
• 651325-80-3 3-bromo-1-(2,4-dimethoxy-phenyl)-propan-1-one 
• 151-10-0 1,3-Dimethoxybenzene 
• 33527-94-5 4-acetoxyiodobenzene 
• 651325-79-0 Acetic acid 4-[(E)-3-(2,4-dimethoxy-phenyl)-3-oxo-propenyl]-phenyl ester 

Downstream Products

• 961-29-5 isoliquirtigenin 
• 63529-06-6 4,2'-dihydroxy-4'-methoxy-trans-chalcone 
• 51828-10-5 2'-methoxyisoliquiritigenin 
• 69097-97-8 7,4'-dihydroxy-dihydroflavone 
• 32274-71-8 7-Methylliquiritigenin 
• 876513-28-9 4-acetoxy-2',4'-dimethoxychalcone 
• 30071-42-2 4-Hydroxy-2',4'-dimethoxy-3,5,5'-trinitro-chalcon 

Relevant academic research and scientific papers

Synthesis and Characterization of a Phosphate Prodrug of Isoliquiritigenin

Isoliquiritigenin (1) possesses a variety of biological activities in vitro. However, its poor aqueous solubility limits its use for subsequent in vivo experimentation. In order to enable the use of 1 for in vivo studies without the use of toxic carriers

Novel insights into the mode of action of vasorelaxant synthetic polyoxygenated chalcones

Polyphenols consumption has been associated with a lower risk of cardiovascular diseases (CVDs) notably through nitric oxide (NO)- and estrogen receptor α (ERα)-dependent pathways. Among polyphenolic compounds, chalcones have been suggested to prevent end

Analogues of xanthones——Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates

Two series of compounds (chalcones and bis-chalcones) were designed, synthesized, and evaluated as α-glucosidase inhibitors (AGIs) with 1-deoxynojirimycin as positive control in vitro. Most of the compounds with two or four hydroxyl groups showed better inhibitory activities than 1-deoxynojirimycin towards α-glucosidase with noncompetitive mechanism. Moreover, most of the hydroxy bis-chalcones exhibit good α-glucosidase inhibitory activities in enzyme test. Inspiringly, bis-chalcones 2g (at 1 μM concentration) has stronger effect than 1-deoxynojirimycin on reducing the glucose level in HepG-2 cells (human liver cancer cell line).

Synthesis of a series of novel dihydroartemisinin monomers and dimers containing chalcone as a linker and their anticancer activity

A new series of monomer and dimer derivatives of dihydroartemisinin (DHA) containing substituted chalcones as a linker were synthesized and investigated for their cytotoxicity in human cancer cell lines HL-60 (leukemia), Mia PaCa-2 (pancreatic cancer), PC

Synthesis, antitubercular activity, and molecular modeling studies of analogues of isoliquiritigenin and liquiritigenin, bioactive components from Glycyrrhiza glabra

Isoliquiritigenin (ISL, 1) and liquiritigenin (LTG, 2) were isolated from the rhizomes of Glycyrrhiza glabra. In an attempt to develop potent and selective antituberculosis agents, a series of ISL analogues were synthesized mainly via acid- and base-catalyzed Claisen-Schmidt condensation reaction for their antitubercular activity. Compared to ISL (MIC = 25 μg/mL), analogues 5, 8, and 10 showed similar antitubercular activity, but, interestingly, 6, 7, and 15 exhibited twofold higher activity (MIC = 12.5 μg/mL) over ISL, against Mycobacterium tuberculosis. Among the LTG derivatives, LTG 4′-acetate and LTG-oxime were found to be as active (MIC = 25 μg/mL) as LTG. It is the first report on antimycobacterial activity of these ISL- and LTG-based derivatives. Molecular docking and in silico ADME studies revealed that compounds 6, 7, and 15 are potent inhibitors of M. tuberculosis H37Rv alanine dehydrogenase and showed compliance with standard parameters of drug likeness.

In vivo anti-diabetic activity of derivatives of isoliquiritigenin and liquiritigenin

Isoliquiritigenin (ISL), a chalcone and liquiritigenin (LTG), a flavonoid found in licorice roots and several other plants. ISL displays antioxidant, anti-inflammatory, antitumor and hepatoprotective activities whereas LTG is an estrogenic compound, acts as an agonist selective for the β-subtype of the oestrogen receptor. Both the phenolics were isolated from the rhizomes of Glycyrrhiza glabra. Five derivatives from ISL and four derivatives from LTG were synthesized. All the compounds were established by extensive spectroscopic analyses and screened through oral glucose tolerance test to gain preliminary information regarding the antihyperglycemic effect in normal Swiss albino male mice. ISL (1), ISL derivatives 3, 4, 5, 7 and LTG derivatives 9 and 10 showed significant blood glucose lowering effect. The structure-activity relationship indicated that the presence of ether and ester groups in ISL and LTG analogues are important for exhibiting the activity. Compounds 1, 4 and 10 were selected for in vivo antidiabetic activity and found to be potential candidates for treatment of diabetes. It is the first report on antidiabetic activity of ISL derivative 4 and LTG derivative 10.

Enone- and chalcone-chloroquinoline hybrid analogues: In silico guided design, synthesis, antiplasmodial activity, in vitro metabolism, and mechanistic studies

Analogues of the previously reported antimalarial hybrid compounds 8b and 12 were proposed with the aim of identifying compounds with improved solubility and retained antimalarial potency. In silico characterization predicted improved solubilities of the analogues, particularly at low pH; they retained acceptable predicted permeability properties but were predicted to be susceptible to hepatic metabolism. These analogues were synthesized and found to exhibit notable in vitro antimalarial activity. Compounds 25 and 27 were the most active of the analogues. In vitro metabolism studies indicated susceptibility of the analogues to hepatic metabolism. There was also evidence of primary glucuronidation for analogues 24-27. Presumed cis-trans isomerism of 12, 22, and 23 under in vitro metabolism assay conditions was also observed, with differences in the nature and rates of metabolism observed between isomers. Biochemical studies strongly suggested that inhibition of hemozoin formation is the primary mechanism of action of these analogues.

A new synthesis of flavonoids via Heck reaction

Several naturally occuring flavonoids have been synthesised following a new proposed method based on the use of the Heck reaction. The key step involves the coupling of an aryl vinyl ketone with an aryl iodide. This procedure affords the flavonoid moiety in a single step.

Synthesis and description of chalcone-like compounds, inhibitors of aldose reductase

A series of hydroxy- and hydroxy-methoxychalcones was synthesized and the inhibitory activity and selectivity of the compounds towards bovine lens aldose reductase (AR) were tested. All the compounds display affinity for AR. The most active proved to be 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)propen-1-one (isoliquiritigenin, IC50= 7.60 μM). The selectivity of this compound was also tested, its inhibitory activity being assayed against glutathione reductase and sorbitol dehydrogenase.

A Novel α-Hydroxydihydrochalcone from the Heartwood of Pterocarpus angolensis D.C.: Absolute Configuration, Synthesis, Photochemical Transformations, and Conversion into α-Methyldeoxybenzoins

The absolute configuration of (αR)-α,2'-dihydroxy-4,4'-dimethoxydihydrochalcone from the heartwood of Pterocarpus angolensis D.C. is established.Its structure is substantiated by synthesis and by photochemical conversion of its α-O-tosyl derivative into an α-tosyloxymethyldeoxybenzoin and hence to the α-methyldeoxybenzoin analogue.The photochemical step also leads, amongst others, to α-hydroxymethyldeoxybenzoin, β-hydroxydihydrochalcone, and 2-benzylbenzofuran-3-one analogues depending on the conditions the photolysis.