Synthesis, biological evaluation, structural–activity relationship, and docking study for a series of benzoxepin-derived estrogen receptor modulators

Development of the β-lactam type molecular scaffold for selective estrogen receptor α modulator action: synthesis and cytotoxic effects in MCF-7 breast cancer cells

“…Fluoro-substituted tamoxifen and cyclofenol derivatives have been investigated as ER-imaging agents for breast cancer 58,59 and we have previously reported the potent ER-binding properties of fluorine-containing benzoxepine type ER antagonists 30 . We now wished to examine the effect of the inclusion of the lipophilic fluorine substituent on the ER activity of the b-lactam ER antagonist compounds 15b and 15c.…”

Benzoxepin derivatives: design, synthesis, and pharmacological evaluation with sedative–hypnotic effect

“…So, compounds 3a-e was prepared from 2 by the Mannich reaction (Scheme 1). In another pathway, aldol condensation of the benzoxepin 2 with the appropriate aryl aldehydes in the presence of acidic medium afforded the corresponding 4-benzylidenbenzoxapin-5-ones 4a-d, (Barrett et al, 2008) (Scheme 2). Moreover, selective bromination of the a ketone with copper (II) bromide in On the other hand, the benzoxazepins containing a condensed-ring system of pyridazinone 11a-c were prepared through multistep reactions.…”

Synthesis and biological evaluation of phenolic 4,5-dihydroisoxazoles and 3-hydroxy ketones as estrogen receptor α and β agonists

“…Although most estrogen target tissues comprise cells expressing both ER isoforms, ERa is predominantly found in reproductive tissues, kidney, liver as well as central nervous system, 9,10 and it is the predominant subtype expressed in breast cancer. 11 On the other hand, ERb is present in many tissues including colon, prostate, testis, ovary, vascular endothelium, and bone. 9,11 There are plenty of examples of subtype-specific compounds 2,4,[9][10][11][12][13][14][15][16][17][18][19][20][21] and recently it has been shown that, for example, raloxifene which is used for the prevention and treatment of osteoporosis, is a relatively ERb-selective SERM.…”