2-Phenylbenzo[b]furans: Synthesis and promoting activity on estrogen biosynthesis

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• 作者：Wenchen Pu^a ; ^b ; Yun Yuan^a ; ^c ; Danfeng Lu^a ; Xin Wang^a ; Hanwei Liu^d ; Chun Wang^a ; Fei Wang^a ; Guolin Zhang^a ; ^{zhanggl@cib.ac.cn" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Estrogen biosynthesis ; 2-Phenylbenzo[b]furan ; Decarboxylative coupling ; McMurry reaction
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2016
• 出版时间：15 November 2016
• 年：2016
• 卷：26
• 期：22
• 页码：5497-5500
• 全文大小：884 K

文摘

Estrogen biosynthesis is pivotal to many physiological processes of human. Aberrant estrogen level is closely related to a variety of diseases, including breast cancer and osteoporosis. Previously we found that 2-phenylbenzo[b]furan glycosides could promote estrogen biosynthesis. To find high active 2-phenylbenzo[b]furans, fifty-four 2-phenylbenzo[b]furans were prepared via four strategies according to corresponding substrate scopes. Biological evaluation in HEK293A cells showed that some compounds exhibited promotive activity on estrogen biosynthesis. 2-(4-Chlorophenyl)-7-methoxybenzo[b]furan possessed the highest activity with EC₅₀ value of 14.68 μM. Furthermore, these compounds did not affect aromatase expression in HEK292A cells, indicating that these 2-phenylbenzo[b]furans might enhance estrogen biosynthesis via directly allosteric regulation of aromatase or indirectly via posttranslational modification.