98314-70-6Relevant academic research and scientific papers
Identification of 10-dehydrooxyglycyuralin E as a selective human estrogen receptor alpha partial agonist
Saito, Nao,Kawase, Keiko,Yamashita, Naoya,Tang, Yingzhan,Wang, Ying,Wang, Jian,Liu, Yongxiang,Li, Ning,Li, Wei,Cheng, Mao-Sheng,Koike, Kazuo,Kanno, Yuichiro,Nemoto, Kiyomitsu
, (2019)
Selective estrogen receptor modulators (SERMs)act as either agonist or antagonist of estrogen receptor (ER)in a tissue selective manner and have been used in several diseases such as breast cancer, postmenopausal syndrome, osteoporosis, and cardiovascular diseases. However, current SERMs may also increase the risk of serious side effects and trigger drug resistance. Herein, a screening program, that was designed to search for novel SERMs, resulted in the identification of a series of 2-arylbenzofuran-containing compounds that are ligands for ERα, when applying the Gaussia-luciferase reporter assay. One of these compounds, 10-dehydrooxyglycyuralin E (T9)was chemically synthesized. T9 showed anti-estrogenic/proliferative activity in ERα-positive breast cancer cells. Pretreatment of T9 prevented the mRNA expression of GREB1, which is an estrogen response gene. Furthermore, by an in silico docking simulation study we demonstrated that T9 showed interactions directly to ERα. Taken together, these results demonstrated that T9 is a candidate of SERMs and a useful seed compound for the foundation of the selective activity of SERMs.
Collective Syntheses of 2-(3-Methylbenzofuran-2-yl)phenol-Derived Natural Products by a Cascade [3,3]-Sigmatropic Rearrangement/Aromatization Strategy
Tang, Yingzhan,Jiang, Chongguo,Zhang, Xinhang,Liu, Chengjun,Lin, Jingsheng,Wang, Yanshi,Du, Chuan,Peng, Xiaoshi,Li, Wei,Liu, Yongxiang,Cheng, Maosheng
supporting information, p. 11102 - 11109 (2017/10/27)
A cascade [3,3]-sigmatropic rearrangement/aromatization strategy to the synthesis of 2-(3-methylbenzofuran-2-yl)phenol derivatives was developed and applied to the collective syntheses of seven 2-arylbenzofuran-containing natural products, namely glycybenzofuran, glycyuralin E, lespedezol A1, puerariafuran, 7,2′,4′-trihydroxy-3-benzofurancarboxylic acid, coumestrol, and 4′-O-methylcoumestrol. Among them, the total syntheses of glycybenzofuran, glycyuralin E, puerariafuran, 7,2′,4′-trihydroxy-3-benzofurancarboxylic acid, and 4′-O-methylcoumestrol were reported for the first time. The practicality of this novel strategy in preparation of the key intermediates was demonstrated by performing the reaction on gram scale and by synthesizing a series of natural products with 2-(3-methylbenzofuran-2-yl)phenol scaffolds in a common strategy.
