Synthesis method of glabridin

A technology of glabridin and a synthetic method, applied in directions such as organic chemistry, can solve problems such as long cycle, and achieve the effects of high total yield, fast and efficient synthesis, and short total route

Active Publication Date: 2019-01-18
SHAANXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Of course, some people obtain licorice through artificial cultivation, but the analysis of the survey results found that geographical distribution, growth years, and artificial intervention are important factors affecting the quality of cultivated licorice. There are few wild ones, and the cycle is long, usually around 4 years

Method used

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  • Synthesis method of glabridin
  • Synthesis method of glabridin
  • Synthesis method of glabridin

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Experimental program
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Embodiment 1

[0025] 1. Add 0.30g (1.85mmol) of 7-hydroxycoumarin into a 10mL round bottom flask, add 3mL of acetonitrile, 0.31mL (2.04mmol) of DBU and 0.32mg (0.00185mmol) of copper chloride dihydrate in turn, at 0°C Slowly add 0.22mL (1.94mmol) of 2-methyl-3-butyn-1-ol, react at room temperature for 10h, and TLC monitors that the reaction of raw materials is complete. Pour the reaction solution into saturated NaHCO 3 In aqueous solution, after extraction with ethyl acetate, over anhydrous MgSO 4 Dry, filter, concentrate under reduced pressure, and separate by column chromatography (eluent: EA / PE=1:3) to obtain compound I (0.37g, yield 90%, white solid, Mp: 253-255°C), reaction equation As follows:

[0026]

[0027] The structural characterization data of the obtained compound I are: 1 H NMR (400MHz, CDCl 3 )δ7.64(d, J=9.2Hz, 1H), 7.36(d, J=8.8Hz, 1H), 7.32(d, J=2.0Hz, 1H), 7.04(dd, J=8.4, 2.0Hz, 1H), 6.28(d, J=9.6Hz, 1H), 2.66(s, 1H), 1.71(s, 6H); HRMS(ESI) m / z: theoretical value ...

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Abstract

The invention discloses a synthesis method of glabridin. According to the method, cheap easy-to-obtain 7-hydroxycoumarin is used as a raw material to react with 2-methyl-3-butyne-1-alcohol for building alkyne ester; then, bromine atoms are introduced into alpha sites of obtained alpha-beta-unsaturated compounds; through seven-step reaction including rearrangement, Szuki coupling as core reactionsfor key intermediate (IV) building, dihydroxy compound obtaining through conjugated double bond reduction, Mitsunobu ether formation and methyl removal, glabridin is fast and efficiently synthesized at the total yield of 20 percent finally. Compared with the prior art, the synthesis method has the following advantages that the raw materials are cheap and can be easily obtained; the total route isshort; the total yield is high; the glabridin can be fast and efficiently synthesized.

Description

technical field [0001] The invention relates to a method for rapidly and efficiently synthesizing glabridin through seven steps from cheap and easy-to-obtain 7-hydroxycoumarin. Background technique [0002] Glycyrrhiza glabra is a perennial herb, mainly distributed in northern Xinjiang, Qinghai, Gansu and other provinces. Its main components are triterpenoid saponins such as glycyrrhizinic acid, glycyrrhetinic acid, and glycyrrhizin, and flavonoids such as liquiritigenin and isoliquiritigenin. Efficacy, can anti-inflammatory, anti-virus, liver protection, inhibit HIV and improve the body's anti-tumor ability. Glabridin, a unique isoflavone compound extracted from Glycyrrhiza glabra, exhibits strong antioxidant activity. Among them, glabridin accounts for about 11% of the total flavonoids in Glycyrrhiza glabra, which has strong anti-oxidation, anti-atherosclerosis, and certain effects of regulating blood lipids and lowering blood pressure. It has been shown in the research ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 柴永海刘爱云谢玉柔张琦
Owner SHAANXI NORMAL UNIV
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