327096-49-1

Upstream product

• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 123-11-5 4-methoxy-benzaldehyde 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 36804-11-2 2,4,6-tri-MOM phloracetophenone 

Downstream Products

• 128864-30-2 4,6-dihydroxy-4'-methoxyaurone 
• 480-43-3 5,7-dihydroxy-2-(4-methoxyphenyl)chroman-4-one 
• 137225-57-1 2',4',6'-trihydroxy-3-methoxychalkone 

Relevant academic research and scientific papers

Design, synthesis, and cholinesterase inhibition assay of liquiritigenin derivatives as anti-Alzheimer's activity

The marine environment is a rich resource for discovering functional materials, and seaweed is recognized for its potential use in biology and medicine. Liquiritigenin has been isolated and identified from Sargassum pallidum. To find new anti-Alzheimer's activity, we designed and synthesized thirty-two 7-prenyloxy-2,3-dihydroflavanone derivatives (3a-3p) and 5-hydroxy-7-prenyloxy-2,3-dihydro-flavanone derivatives (4a-4p) as cholinesterases inhibitors based on liquiritigenin as the lead compound. Inhibition screening against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) indicated that all synthesized compounds possessed potent AChE inhibitory activity and moderated to weak BuChE inhibitory activity in vitro. Kinetic studies demonstrated that compound 4o inhibited AChE via a dual binding site ability. In addition, all compounds displayed the radical scavenging effects. Finally, the molecular docking simulation of 4o in AChE active site displayed good agreement with the obtained the pharmacological results.

Biological Properties and Absolute Configuration of Flavanones From Calceolaria thyrsiflora Graham

Flavanones (–)-(2S)-5,4’-dihydroxy-7-methoxyflavanone (1) and (–)-(2S)-5,3’,4’-trihydroxy-7-methoxyflavanone (2) were isolated from the extracts of Calceolaria thyrsiflora Graham, an endemic perennial small shrub growing in the central zone of Chile. The absolute configuration of these compounds was resolved by optical rotation experiments and in silico calculations. Three analogs (3, 4, and 5) were synthesized to do structure-activity relationships with the biological assays studied. Biological tests revealed that only flavanone 2 exhibited a moderate inhibitory activity against the methicillin-resistant strain S. aureus MRSA 97-77 (MIC value of 50 μg/ml). In addition, flavanone 2 showed a potent, selective, and competitive inhibition of 5-hLOX, which supports the traditional use of this plant as an anti-inflammatory in diseases of the respiratory tract. Also, 2 exhibited cytotoxic and selective effects against B16-F10 (8.07 ± 1.61 μM) but 4.6- and 17-fold lesser activity than etoposide and taxol.

A kind of A ring with methyl of [...] compound, preparation method and anti-inflammatory activity

The invention discloses a quinoid chalcone compound with a methyl group at an A ring, and a preparation method and anti-inflammatory activity thereof. The compound has a structure as shown in a general formula (I) which is described in the specification. The preparation method comprises the following steps: (1) synthesizing 2-hydroxy-4,6-dimethoxyacetophenone; (2) synthesizing 2'-hydroxy-4',6'-dimethoxychalcone derivative; (3) synthesizing 2',4',6'-trihydroxy chalcone derivative; and (4) synthesizing the quinoid chalcone compound with a methyl group at the A ring. The compound is simple to prepare and has obvious anti-inflammatory action.

Synthesis and biological evaluation of 5,7-dihydroxyflavanone derivatives as antimicrobial agents

A series of 5,7-dihydroxyflavanone derivatives were efficiently synthesized. Their antimicrobial efficacy on Gram-negative, Gram-positive bacteria and yeast were evaluated. Among these compounds, most of the halogenated derivatives exhibited the best antimicrobial activity against Gram-positive bacteria, the yeast Saccharomyces cerevisiae, and the Gram-negative bacterium Vibrio cholerae. The cytotoxicities of these compounds were low as evaluated on HepG2 cells using a cell viability assay. This study suggests that halogenated flavanones might represent promising pharmacological candidates for further drug development.

Design, synthesis and antidepressant activity evaluation 2′-hydroxy-4′,6′-diisoprenyloxychalcone derivatives

In this study, 14 2′-hydroxy-4′,6′-diisoprenyloxychalcone compounds were synthesized and their antidepressant activities were evaluated using the forced swimming test. The pharmacological results showed that six compounds significantly reduced immobility times during the forced swimming test at a dose of 10 mg/kg, indicative of antidepressant activity. Among these, three compounds (4d, 4e, and 4g) exhibited better antidepressant activity, with reduced immobility time by 38.3, 34.0, and 27.4 %, respectively. For explanation of the putative mechanism of action, compounds 4e, 4g were tested in chemical induced models.

Synthesis and studies on antidepressant activity of 2′,4′, 6′-trihydroxychalcone derivatives

In this study, we synthesized a series of 2′,4′,6′- trihydroxychalcone derivatives and evaluated their antidepressant activities. The results of the nine compounds showed significantly reduced times during the forced swimming test at a dose of 10 mg/kg, indicative of antidepressant activity. Among the compounds, 2-bromo-2′,4′,6′- trihydroxychalcone (3h) was found to be the most potent, and it was observed that compound 3h at dose of 10, 20, and 40 mg/kg significantly reduced the duration of immobility times in the FST and TST in mice 30 min after treatment. Springer Science+Business Media, LLC 2011.

A one-pot synthesis of aurones from substituted acetophenones and benzaldehydes: A concise synthesis of aureusidin

A one-pot synthesis of aurones from substituted acetophenone and benzaldehyde has been developed on the basis of an improved Algar-Flynn-Oyamada reaction. By using this method, several aurones were prepared in three steps from commercial starting materials. The usefulness of this one-pot strategy was confirmed by a synthesis of aureusidin, an inhibitor of iodothyronine deiodinase, in 41% overall yield. In comparison with a two-step synthesis of this product from the same substrates, the one-pot strategy was more effective, giving a higher yield and requiring fewer and simpler operations. Georg Thieme Verlag Stuttgart New York.

Synthesis and studies on antidepressant effect of 5,7-Dihydroxyflavanone derivatives

A series of 5,7-dihydroxyflavanone derivatives were synthesized and evaluated their antidepressant activities. The results showed that of nine compounds significantly reduced times during the forced swimming test at a dose of 10 mg/kg, indicative of antidepressant activity. Among the compounds, 4o (4'-methoxy-5,7,3'-trihydroxyflavanone) was found to be the most potent and it was observed that the compound 4o at dose of 10, 20 and 40 mg/kg significantly reduced the duration of immobility times in the Forced swimming test in mice 0.5 h after treatment.

TWO NEW PRENYLAURONES, ANTIARONES A AND B, FROM THE ROOT BARK OF ANTIARIS TOXICARIA LESCH.

Two new prenylated aurones, antiarones A and B, were isolated from the root bark of Antiaris toxicaria Lesch.On the basis of spectral evidence, the structures of antiarones A and B were shown to be 1 and 2, respectively.These two compounds are the first e