69097-97-8

Usage

Uses

Used in Pharmaceutical Industry:
7-Hydroxy-2-(p-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-3-one is used as a key compound in the preparation of liquiritigenin/isoquiritigenin derivative compounds for the treatment of cholestatic liver disease. Its unique structure and biological properties make it a promising candidate for the development of novel therapeutic agents targeting liver-related disorders.
In the pharmaceutical industry, (±)-Liquiritigenin is utilized for its potential therapeutic effects on cholestatic liver disease, a condition characterized by impaired bile flow and liver damage. 7-Hydroxy-2-(p-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-3-one's ability to modulate cellular signaling pathways and exhibit anti-inflammatory and antioxidant properties makes it a valuable component in the development of new drugs and treatment strategies for liver-related disorders.

Upstream product

• 961-29-5 isoliquirtigenin 
• 7664-93-9 sulfuric acid 
• 551-15-5 liquiritin 
• 23423-35-0 (E)‐3‐(4‐hydroxyphenyl)‐1‐(2,4‐dimethoxyphenyl)prop‐2‐en‐1‐one 
• 123-08-0 4-hydroxy-benzaldehyde 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 1085453-61-7 ethyl 4-(triisopropylsilyloxy)benzoate 
• 2196-14-7 7,4'-Dihydroxyflavon 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 13745-20-5 2',4,4'-trihydroxychalcone 
• 108-46-3 recorcinol 
• 128837-26-3 4-(ethyloxymethoxy)benzaldehyde 
• 20034-62-2 2'-Hydroxy-4'-(aethoxy-methoxy)-acetophenon 

Downstream Products

• 24672-86-4 7-hydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)chroman-4-one 
• 78316-25-3 5,7,3',4’-tetrahydroxy-6,8-di-C-prenylflavanone 
• 78316-27-5 (+/-)-bavachin 
• 78316-26-4 4'-hydroxy-7-O-prenylflavanone 
• 486-66-8 daidzein 
• 131887-80-4 (2R,3S)-2,7,4'-trihydroxyisoflavanone 
• 485-72-3 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 486-63-5 isoformononetin 
• 109963-62-4 2,7,4'-trihydroxyisoflavanone 
• 1239578-51-8 2-(7-hydroxy-2-(4-hydroxyphenyl)chroman-4-ylidene)hydrazinecarbothioic O-acid 
• 59870-65-4 Glabrol 
• 59870-65-4 glabrol 
• 101097-68-1 liquiritigenin oxime 

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.

Synthesis and studies of flavone and bis-flavone derivatives

Flavonoids are widely occurring polyphenols of plant origin and well explored in the field of pharmacological activities. Recent studies showed this scaffold to be more dynamic as fluorescent probe. Very rare reports are there in literature on flavones as liquid crystals, for the first time we have synthesized and characterized flavone and bis-flavone derivatives for mesomorphic properties. Compounds 9a–d and 13a–d were studied for liquid crystalline properties by Differential scanning calorimetry (DSC) and Polarizing optical microscopy (POM) studies. The compounds 8, 9a–d, 12, and 13a–d were also studied for antioxidant property by DPPH assay.

A method of synthesizing the glycyrrhizin (by machine translation)

The invention relates to a synthetic chemical method of glycyrrhizin. In order to 2, 4 - dihydroxy acetophenone and 4 - hydroxy benzoic acid ethyl ester as the raw material, the protective group for a hydroxyl, keto ester condensation, cyclization and hyd

METHOD FOR PRODUCING LIQUIRITIGENIN PRECURSOR

PROBLEM TO BE SOLVED: To provide a method which is suitable as a mass production method of liquiritigenin. SOLUTION: Provided is a method for producing liquiritigenin, comprising: synthesizing and crystallizing a trialkoxy-isoliquiritigenin represented by a formula (iii) by coupling a 4-alkoxycinnamic acid represented by a formula (i) and a 1,3-alkoxybenzene represented by a formula (ii) by a Friedel-Craft reaction (A); and eliminating a protective group to obtain isoliquiritigenin represented by a formula (iv). The isoliquiritigenin represented by a formula (iv) is administered in a body as a precursor of liquiritigenin represented by a formula (v), which is converted to a (-) form of liquiritigenin in the body. COPYRIGHT: (C)2016,JPOandINPIT

In vitro and in vivo synergistic interaction of substituted chalcone derivatives with norfloxacin against methicillin resistant Staphylococcus aureus

Thirty chalcone derivatives were synthesized via a base catalyzed Claisen Schmidt condensation and evaluated for their anti-methicillin-resistant Staphylococcus aureus (MRSA) activity alone and in combination with norfloxacin. Among these, 5 derivatives namely trans-3-(1H-indol-3-yl)-1-(4′-benzyloxyphenyl)-2-propen-1-one (2), 1-(4″-biphenyl)-3-(3′4′-dihydroxyphenyl)-2-propen-1-one (11), 1-(4″-hydroxy-3″-methylphenyl)3-(4′-hydroxyphenyl)-2-propen-1-one (14), 3-(4′-chlorophenyl)-1-(4″-hydroxyphenyl)2-propen-1-one (17), and LTG-oxime (27) showed significant antibacterial activity with MIC 12.5-50 g mL-1 respectively. In combination studies, derivatives 2 and 14 significantly reduced the MIC of norfloxacin by up to 16 fold (FICI 0.5), while derivatives 11, 17 and 27 reduced it by up to eight fold (FICI ≤ 0.5). Flow cytometry analysis results clearly indicated that derivatives 2 and 14 significantly promote the accumulation and inhibition of the Et-Br efflux, which was further validated through spectrofluorimeter using clinical isolate MRSA-ST2071. In systemically infected Swiss albino mice model, both the compounds significantly (P 0.001, P 0.01) lowered the systemic bacterial load in blood, liver, kidney, lung and spleen tissues. This study supports the promising use of chalcones in the development of economical antibacterial combinations.

Synthesis of oxygenated 4-arylisoflavans and 4-arylflavans

Oxygenated 4-arylisoflavans and 4-heteroarylisoflavans were synthesized in good yields via BF3·OEt2 catalyzed arylation reactions of 4′,7-diacetoxyisoflavan-4-ol 8 with activated aryl and heteroaryl compounds. These reactions were found to produce stereoselectively the trans isomers. Similar reactions of 4′,7-diacetoxyflavan-4-ol 16 afforded the corresponding 4-arylflavans and 4-heteroarylflavans as mixtures of cis/trans isomers.

Synthesis of oxygenated 4-arylisoflavans and 4-arylflavans

Oxygenated 4-arylisoflavans and 4-heteroarylisoflavans were synthesized in good yields via BF3·OEt2 catalyzed arylation reactions of 4′,7-diacetoxyisoflavan-4-ol 8 with activated aryl and heteroaryl compounds. These reactions were found to produce stereoselectively the trans isomers. Similar reactions of 4′,7-diacetoxyflavan-4-ol 16 afforded the corresponding 4-arylflavans and 4-heteroarylflavans as mixtures of cis/trans isomers.

An efficient catalytic synthesis of flavanones under green conditions

An efficient and "green" catalytic conversion of 2′-hydroxychalcones to flavanones in 15 min in the presence of a simple amino acid and a base at room temperature is reported. Liquiritigenin was also efficiently synthesised under these conditions.

Cloning and functional characterization of a chalcone isomerase from trigonella foenum-graecum L

Flavonoids belong to a group of plant natural products with variable phenolic structures and play important roles in protection against biotic and abiotic stress. Fenugreek (Trigonella foenum-graecum L.) seeds and stems contain flavonol glycosides and isoflavone derivatives. Up to now, the molecular features of fenugreek flavonoid biosynthesis have not been characterized. Here we present cloning of a cDNA encoding a chalcone isomerase (namely TFGCHI1) from the leaves of T. foenum-graecum which convert chalcones to flavanones in vitro. Transformation of Arabidopsis loss-of-function tt5 (chi) mutant with a TFGCHI1 cDNA complemented tt5 and produced higher levels of flavonol glycosides than wild-type Col-0. Georg Thieme Verlag KG Stuttgart · New York.

Synthesis and antitumoractivity of liquiritigenin thiosemicarbazone derivatives

In an attempt to develop potent and selective antitumor agents,a series of liquiritigenin thio-semicarbazone derivatives were designed and synthesized. The cytotoxicities of these compounds were evaluated in vitro against K562,DU-145,SGC-7901,HCT-116 and Hela cell lines. The pharmacological results showed that most of the prepared compounds displayed excellent selective cytotoxicity toward K562 and DU-145 cells. From the structureeactivity relationships we may conclude that the introduction of a thiosemicarbazone functional group at the 4-position in the skeleton of liquiritigenin is associated with an increase in cytotoxicity.