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
ANALOGS OF THE NATURAL PRODUCT ICARIIN
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Paragraph 00168; 00192, (2020/03/02)
Provided herein are analogs of the natural product icariin represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof. The analogs can be used to modulate (e.g., inhibit, such as by competitive inhibition) PDE5 and thereby treat a wide range of PDE5- mediated diseases, including cardiovascular, gastrointestinal, pulmonary, musculoskeletal, neurological and reproductive diseases. Also provided herein are compositions and methods including compounds of Structural Formula (I).
Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis
Zheng, Yuanyuan,Pu, Wenchen,Li, Jiao,Shen, Xianyan,Zhou, Qiang,Fan, Xin,Yang, Sheng-Yong,Yu, Yamei,Chen, Qiang,Wang, Chun,Wu, Xin,Peng, Yong
, p. 130 - 134 (2018/11/30)
Peptidyl-prolyl cis-trans isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (AF-39) was identified as a novel Pin1 inhibitor. Biochemical tests indicate that AF-39 potently inhibits Pin1 activity with an IC50 values of 1.008 μm, and also displays high selectivity for Pin1 among peptidyl prolyl isomerases. Furthermore, AF-39 significantly suppresses cell proliferation of HCC cells in a dose- and time-dependent manner. Mechanistically, AF-39 regulates the subcellular distribution of XPO5 and increases miRNAs biogenesis in HCC cells. This work provides a promising lead compound for HCC treatment, highlighting the therapeutic potential of miRNA-based therapy against human cancer.