Novel steroidal pure antiestrogens
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In silico study of molecular mechanisms of action: Estrogenic disruptors among phthalate esters
2019, Environmental PollutionCitation Excerpt :Conversely, SERMs block the AF-2 activity with H12 relocating into the coactivator-binding cleft (Nettles and Greene, 2005; Paul et al., 2003; Pike et al., 2001). Moreover, the binding of pure antagonists results in the complete destabilization of H12 because of their bulky alkyl chains (Bowler et al., 1989; Pike et al., 2001; Wakeling et al., 1991). The MD simulations show the conformation changes of hERα in the apo state when binding the different PAEs-type ligands (Figs. S1–S3).
Selective estrogen receptor modulators (SERMs) and selective estrogen receptor degraders (SERDs) in cancer treatment
2018, Pharmacology and TherapeuticsCitation Excerpt :It was observed that pure antiestrogenicity resulted from compounds whose chain lengths at the 7α position were anywhere between 15–19 atoms, long enough to interact with the coactivator binding groove. Side chains with 13–14 carbon atoms either resulted in agonist or SERM activity (Bowler, Lilley, Pittam, & Wakeling, 1989; Hilmi et al., 2012; Traboulsi, El Ezzy, Gleason, & Mader, 2017). The side chain of ICI 164,384 was shown to abolish the association between H12 and the rest of the LBD, preventing the receptor from adopting an agonist or an antagonistic conformation highlighting the unique mode of action of pure antiestrogens (Pike et al., 2001).
Optimization of the alkyl side chain length of fluorine-18-labeled 7α-alkyl-fluoroestradiol
2016, Nuclear Medicine and BiologyFluorinated steroids and their derivatives
2016, Journal of Fluorine ChemistryCitation Excerpt :DAST often replaces the hydroxyl-function with an inversion of configuration [31] as can be seen in the conversion of 73–74 (Scheme 18). DAST has been used to prepare fluorinated bile acid derivatives [31], eg. of type 76, en route to fluorinated squalamines 77 (Scheme 19). As substitution with DAST proceeds via SN2-mechanism, cases have been known, where the OH group on the steroidal framework could not be replaced by a fluoro substituent when using DAST because of steric reasons [32].
Design, synthesis and evaluation of antiestrogen and histone deacetylase inhibitor molecular hybrids
2015, Bioorganic and Medicinal Chemistry