59870-70-1

Upstream product

• 77-78-1 dimethyl sulfate 
• 59870-68-7 glabridin 
• 74-88-4 methyl iodide 
• 105705-54-2 2',4'-dimethoxy-6'',6''-dimethylpyrano<2'',3'':7,8>isoflavanone 
• 17715-69-4 1-Bromo-2,4-dimethoxybenzene 
• 92741-82-7 1,3-diethyl 2-(2,4-dimethoxyphenyl)propanedioate 
• 31042-20-3 7-(benzyloxy)chroman-4-one 
• 124093-43-2 Acetic acid 7-benzyloxy-2H-chromen-4-yl ester 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 76240-27-2 7-hydroxy-2,3-dihydro-4H-chromen-4-one 

Downstream Products

• 59870-68-7 glabridin 

Relevant academic research and scientific papers

In vitro antiproliferative activity of glabridin derivatives and their in silico target identification

Novel Mannich base derivatives of glabridin were synthesized and their antiproliferative activity were performed along with our previously reported glabridin-chalcone hybrids molecules (GCHMs) against various human cell lines MDA-MB-231 (breast adenocarcinoma), HEK-293 (embryonic kidney cell line), K562 (leukemia), MCF-7 (breast adenocarcinoma), HeLa (cervix adenocarcinoma), HepG2 (hepatocellular carcinoma) and WRL-68 (hepatic carcinoma). The result showed that the glabridin significantly reduced cell proliferation with IC50 ranges from 3.67 to 58.30 μM against all the tested cell lines. The remarkable reduction in antiproliferative activity 2’,4’-dimethoxyglabridin and GCHMs compounds with phenolic OH groups protected by methoxy (OCH3) groups suggested that the free OH groups are essential factor for the antiproliferative activity of glabridin and its derivatives. The Mannich base derivatives of glabridin showed moderate activity IC50 (2.20–>95.78 μM). Furthermore, in silico target identification analysis revealed that AKT1, DECR1 and NOS1 are the potential targets for glabridin and their derivatives.

Glabridin-chalcone hybrid molecules: Drug resistance reversal agent against clinical isolates of methicillin-resistant Staphylococcus aureus

A novel series of glabridin-chalcone hybrid molecules (GCHMs) were synthesized and evaluated for their antibacterial and resistance reversal activity against clinical isolates of a methicillin-resistant strain of Staphylococcus aureus (MRSA) alone and in combination with norfloxacin. Glabridin showed significant anti-staphylococcal activity against various MRSA clinical isolates with MICs of 12.5 μg ml-1. However, all its synthesized derivatives displayed moderate to weak activity (MICs ranging from 12.5 to >100 μg ml-1). Among all the synthesized hybrid molecules, compounds 6f, 6h, 8f and 8h along with glabridin were chosen for combination study with norfloxacin. Among all tested compounds, 8h exhibited marked synergism and up to 16-fold reduction in MICs with norfloxacin (FICI range from 0.312 to 0.375). In a systemically infected Swiss albino mice model, compound 8h significantly (p 0.01, p 0.05) lowered the systemic bacterial load in blood, liver, kidney, lung and spleen tissues. The present study reports the potential use of GCHMs in the development of economical anti-infective combinations for the treatment of infection caused by clinical MRSA isolates.

Method for synthesizing optically pure glabridin

The invention relates to a method for synthesizing optically pure glabridin. According to the method, chiral carbon of optically pure glabridin is constructed through biological enzyme catalysis, optically pure glabridin is prepared in combination with an organic synthesis method, and the key steps are that a chiral intermediate compound III is generated by using a lipase catalysis compound II, and an important intermediate compound IV is obtained through a bromination reaction. According to the method for synthesizing optically pure glabridin, raw materials are cheap and easy to obtain, and the total yield is high.

Method for asymmetrically synthesizing glabridin with optical purity

The invention discloses a method for asymmetrically synthesizing glabridin with optical purity, belonging to the field of organic synthesis. According to the invention, 7-hydroxychroman-4-one is usedas a raw material and is subjected to seven successive reactions including a protecting group protection reaction, an enol esterification reaction, an asymmetric addition reaction, a carbonyl reduction reaction, a phenolic hydroxyl protecting group removal reaction, a cyclization reaction and a demethylation reaction so as to finally prepare glabridin with optical purity. The optically pure glabridin is obtained by asymmetrically introducing a chiral center by using a palladium catalyst and an organophosphorus ligand; reaction conditions are mild; operation is convenient; and the method is suitable for industrial application. The raw material is easy to obtain and low in cost, and the product is good in yield and high in stereoselectivity.

Method for asymmetrically synthesizing glabridin with optical purity under catalysis of ruthenium compound

The invention relates to a method for asymmetrically synthesizing glabridin with optical purity under catalysis of a ruthenium compound. The method comprises the following steps: 1) taking isoflavoneprotected by a protection group as a raw material and carrying out dynamic kinetic asymmetric hydrogen transfer reaction under the catalysis effect of a ruthenium trichloride compound and the action of an acid-alkali buffering system to obtain chiral isoflavol with an absolute configuration being (3R, 4R); 2) removing hydroxyl of the chiral isoflavol under the action of triethylsilane and trifluoroacetic acid to obtain a product with an absolute configuration being (R); 3) removing a protection group of the product with the configuration being (R) in step 2) under an acidic or alkaline condition to obtain the glabridin with the configuration (R) and the optical purity. The method provided by the invention can be used for synthesizing the glabridin with the optical purity in a high-yield and high-stereoselectivity manner; the obtained product is completely the same as that of the glabridin extracted from glycyrrhiza glabra and can be used for replacing the glabridin derived from naturalplants to be industrially applied.

A MANUFACTURING PROCESS OF ISOFLAVAN OR ISOFLAVENE DERIVATIVES

The present invention relates to a method of synthesizing isoflavan and isoflavene derivatives of the Formula 1, which have the biological efficacy of antioxidation and protection against ultraviolet light. The method is effective and suitable for a mass production of isoflavan and isoflavene derivatives, which is a more convenient alternative preparation method compared to the isolation method by the extraction of plants, such as licorice, via troublesome preparative processes.