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Discovery of thiochroman and chroman derivatives as pure antiestrogens and their structure-activity relationship.

Abstract：

:In order to develop pure antiestrogens, a series of 7-hydroxy-3-(4-hydroxyphenyl)-3-methylchroman and 7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman derivatives with sulfoxide containing side chains at the 4-position were designed, synthesized, and evaluated. Among them, compounds 14b and 24b functioned as pure antiestrogens with the ability to downregulate ER, and their in vitro and in vivo antiestrogen activities were similar to those of ICI182,780. In addition, the structure-activity relationship indicated that the (3RS,4RS)-configuration between the 3- and 4-position, the methyl group at the 3-position, the 9-methylene chain between the scaffold and the sulfoxide moiety, and the terminal perfluoroalkyl moiety play an important role in increasing estrogen receptor binding and oral antiestrogen activities.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Kanbe Y,Kim MH,Nishimoto M,Ohtake Y,Kato N,Tsunenari T,Taniguchi K,Ohizumi I,Kaiho S,Morikawa K,Jo JC,Lim HS,Kim HY

doi

10.1016/j.bmc.2006.03.020

subject

Has Abstract

pub_date

2006-07-15 00:00:00

pages

4803-19

issue

14

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(06)00221-5

journal_volume

14

pub_type

杂志文章

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