122566-22-7Relevant articles and documents
Synthesis of novel estrogen receptor antagonists using metal-catalyzed coupling reactions and characterization of their biological activity
Jiang, Xiang-Rong,Wang, Pan,Smith, Carolyn L.,Zhu, Bao Ting
, p. 2779 - 2790 (2013/06/05)
Estrogen receptor (ER) antagonists are valuable in the treatment of ER-positive human breast cancer. In this study, we designed and synthesized nine new derivatives of 17β-estradiol (E2) with a bulky side chain attached to its C-7α position, and determined their ER antagonistic activity using in vitro bioassays. Four of the derivatives showed a strong inhibition of ERα transactivation activity in a luciferase reporter assay and blocked ERα interactions with coactivators. Similarly, these derivatives also strongly inhibited the growth of the ERα-positive human breast cancer cells. Computational docking analysis was conducted to model the interaction of these antagonists with the human ERα and showed that they could tightly bind to the ERα in a manner similar to that of ICI-182,780, a pure ER antagonist. These results provide an example that attachment of a bulky side chain to the C-7α position of E2 can produce ER antagonists with ER affinity comparable to that of ICI-182,780.
Jostling for position: Optimizing linker location in the design of estrogen receptor-targeting PROTACs
Cyrus, Kedra,Wehenkel, Marie,Choi, Eun-Young,Lee, Hyosung,Swanson, Hollie,Kim, Kyung-Bo
scheme or table, p. 979 - 985 (2011/02/21)
Estrogen receptor-α (ER) antagonists have been widely used for breast cancer therapy. Despite initial responsiveness, hormone-sensitive ER-positive cancer cells eventually develop resistance to ER antagonists. It has been shown that in most of these resis
C6-(N,N-butyl-methyl-heptanamide) derivatives of estrone and estradiol as inhibitors of type 1 17β-hydroxysteroid dehydrogenase: Chemical synthesis and biological evaluation
Cadot, Christine,Laplante, Yannick,Kamal, Fatima,Luu-The, Van,Poirier, Donald
, p. 714 - 726 (2007/10/03)
A series of estrone and estradiol derivatives having an N-butyl,methyl heptanamide side chain at C6-position were synthesized, tested as inhibitors of type 1 17β-HSD and assessed for their possible estrogenic activity. A better type 1 17β-HSD inhibition w