118525-40-9Relevant articles and documents
Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen - Cope rearrangement
Mei, Qinggang,Wang, Chun,Zhao, Zhigang,Yuan, Weicheng,Zhang, Guolin
, p. 1220 - 1225 (2015)
The hemisynthesis of the naturally occurring bioactive flavonoid glycoside icariin (1) has been accomplished in eleven steps with 7% overall yield from kaempferol. The 4?-OH methylation of kaempferol, the 8-prenylation of 3-O-methoxymethyl-4?-O-methyl-5- O-prenyl-7-O-benzylkaempferol (8) via para-Claisen-Cope rearrangement catalyzed by Eu(fod)3 in the presence of NaHCO3 , and the glycosylation of icaritin (3) are the key steps.
Magnesium dicarboxylates promote the prenylation of phenolics that is extended to the total synthesis of icaritin
Fu, Xuewen,Lu, Xiaoxia,Wang, Chun,Wen, Yongju,Xiong, Wei,Zhang, Guolin,Zhang, Jichao
, p. 1117 - 1124 (2022/02/16)
The prenylation of phenolic substrates promoted by magnesium dicarboxylates was developed. An investigation of the scope demonstrated that substrates with electron-donating group(s) gave better yields than those with electron-withdrawing group(s). Althoug
Convenient and efficient total synthesis method for icaritin and derivatives of icaritin
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Paragraph 0063; 0084-0088, (2020/02/06)
The invention belongs to the field of natural medicine synthesis and particularly relates to a convenient and efficient total synthesis method for icaritin and derivatives of icaritin. The specific technical scheme is as follows: 2'-hydroxyacetophenone and benzaldehyde are used as raw materials, firstly, isopentene groups are introduced in aromatic rings of raw materials under the catalysis of anorganic polyacid metal ion complex, a flavonol framework is constructed under mild and green conditions, and an isopentenyl flavone compound comprising the icaritin and derivatives of icaritin is further synthesized. The method effectively overcomes the limitation of poor substrate solubility and poor regioselectivity when flavone is constructed firstly and then isopentene groups are introduced, the problems of frequent introduction and removal of protecting groups in a conventional isopentenylation method are solved, and the synthesis route is greatly simplified; and meanwhile, the problems of complex products and more byproducts in an isopentene group rearrangement method are solved. The total synthesis method provided by the invention is mild in condition, convenient to operate, high intotal yield and suitable for mass production of the isopentenyl flavone compound.
Preparation and medical application methods of icaritin derivative
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, (2019/10/23)
The invention relates to preparation and medical application methods of an icaritin derivative. The preparation method comprises taking trihydroxyacetophenone, chloromethyl methyl ether and the like as initial raw materials to connect isopentene groups to an 8th carbon through vicinal rearrangement, then performing serial reaction of formation of a flavone framework, and lastly, performing dehydration to introduce propylene groups to synthesize the icaritin derivative. The preparation method of the icaritin derivative is low in the cost of the synthetic routes, simple in operation, high in recovery rate and applicable to industrial production. Pharmacological effect experiments prove that the icaritin derivative has the pharmacological effect of activating organism endogenous stem cells and achieves the rehabilitation function of repair traumatic pathological changes of blood vessels, nerves, endothelial cells and matrixes and can be applied to preparing drugs for repairing traumatic pathological changes of tissues, thereby having a good prospect in fields such as drugs for rehabilitation of pathological changes of erectile dysfunction.