title: 2-Phenylbenzo[b]furans: Synthesis and promoting activity on estrogen biosynthesis.
abstract: 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 EC50value of 14.68μM. 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.
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China; University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Wenchen
authors.initials: W
authors.lastname: Pu
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China; School of Materials and Science Engineering, Southwest University of Science and Technology, Mianyang 621010, China.
authors.forename: Yun
authors.initials: Y
authors.lastname: Yuan
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Danfeng
authors.initials: D
authors.lastname: Lu
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Xin
authors.initials: X
authors.lastname: Wang
authors.affiliation: Ningbo Entry-Exit Inspection and Quarantine Bureau Technical Center, Ningbo 315012, China.
authors.forename: Hanwei
authors.initials: H
authors.lastname: Liu
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Chun
authors.initials: C
authors.lastname: Wang
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Fei
authors.initials: F
authors.lastname: Wang
authors.affiliation: Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China. Electronic address: zhanggl@cib.ac.cn.
authors.forename: Guolin
authors.initials: G
authors.lastname: Zhang
mesh_terms: D001141:Aromatase / Q000378:metabolism; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D053898:Biosynthetic Pathways / Q000187:drug effects; D004967:Estrogens / Q000819:agonists* / Q000378:metabolism*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D057809:HEK293 Cells; D006801:Humans
chemical_list: D001555:Benzene Derivatives; D004967:Estrogens; D005663:Furans; D001141:Aromatase
keywords: 2-Phenylbenzo[b]furan; Decarboxylative coupling; Estrogen biosynthesis; McMurry reaction