Method for synthesizing fisetin

Abstract

The invention discloses a method for synthesizing fisetin, which comprises the following steps: by taking paeonol and veratraldehyde as raw materials, carrying out condensation reaction on the paeonol and the veratraldehyde under the action of a basic catalyst, carrying out cyclization reaction on a condensation product through hydrogen peroxide, obtaining crude fisetin through hydrogen bromide, recrystallizing with an ethanol solution, and drying to obtain the fisetin. And finally, high-quality fisetin is obtained. The raw materials used in the invention are cheap and easily available, the two raw materials are natural products, nontoxic and safe, and the synthesis process is simple and convenient; the condensation reaction is carried out at room temperature, so that the reaction procedures are greatly simplified, the synthesis steps are reduced, and the whole reaction time can be controlled within 30 hours; the raw material conversion rate is high, the yield exceeds 82.4%, the product purity is 99.1% or above, the quality is stable, ethanol is mainly used in the synthesis process, other toxic and harmful organic solvents are not used, a green, environment-friendly and energy-saving synthesis path is created, and the method is most suitable for large-scale production of small and medium-sized enterprises.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a method for synthesizing fisetin. Background technique [0002] The chemical name of Fisetin is 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-benzofuran-4-one, also known as 3,3',4', 7-Tetrahydroxyflavone, molecular structure formula is Fisetin is a natural flavonoid compound with good pharmacological activity, which can improve the damage of retinal pigment epithelial cells, eliminate ultraviolet-induced cell death and oxygen free radicals, prevent cataracts, regulate the production of vascular endothelial production factors, and treat rheumatoid Arthritis and inhibit the proliferation of prostate cancer, breast cancer, cervical cancer, blood cancer and other cells and promote their apoptosis, with significant anti-tumor, anti-inflammatory, anti-oxidation, anti-coagulation, anti-thrombotic, antispasmodic and other pharmacological effects It can also treat diabetic kidney d...

AI Technical Summary

Problems solved by technology

[0006] In conclusion, the current problems in the synthesis of fisetin are: (1) there are still few literatures to try and explore the synthesis of fisetin, and there are fewer relatively mature synthetic techniques of fisetin; (2) mainly 2,4-di Hydroxyacetophenone is raw material, and synthetic step is many, and with long time, complex reaction system, productive rate is generally on the low side; (3) the used solvent of reaction is of a great variety, has used some unsafe reagents, as trifluoromethanesulfonic anhydride , p-toluenesulfonic acid, pyridine, chloromethyl methyl ether, 1,4-dioxane, diethyl ether, and palladium-carbon catalysis in the reactor, etc., are not suitable for large-scale production applications in factories; (4) hydroxyl groups need to be protected, The reaction process is lengthy, and two column chromatography separations are required, and the quality of the product is unstable; (5) Some synthesis processes need to last for more than 80 hours, and temperature control is required to heat and reflux, which requires high synthesis equipment and high production costs

Images