ArticleChemMedChem2017
Selenophenes: Introducing a New Element into the Core of Non-Steroidal Estrogen Receptor Ligands.
Article in ChemMedChem, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 26 citations in OpenAlex.
- Bioisostere-Driven Discovery of SePP: A Selenium-Containing Polypharmacological Agent Relevant to Fragile X Syndrome.Journal of medicinal chemistry · 2026Article
- A selenium-containing selective estrogen receptor modulator to overcome drug resistance of chronic myeloid leukemia.Apoptosis : an international journal on programmed cell death · 2026Article
- Silver-Mediated Electrosynthesis of Substituted Isoquinolines via Cyclization of 2‑Ethynylbenzaldehydes.ACS omega · 2025Article
- Design, synthesis, and biological evaluation of novel 3-aryl-4-(3,4,5-trimethoxyphenyl)selenophene derivatives as new tubulin inhibitors.Journal of enzyme inhibition and medicinal chemistry · 2025Article
- Design and radiosynthesis of class-IIa HDAC inhibitor with high molar activity via repositioning theScientific reports · 2024Article
- Novel late-stage radiosynthesis of 5-[18F]-trifluoromethyl-1,2,4-oxadiazole (TFMO) containing molecules for PET imaging.Scientific reports · 2021Article
- Synthesis of 3,4-Bis(Butylselanyl)Selenophenes and 4-Alkoxyselenophenes Promoted by OxoneMolecules (Basel, Switzerland) · 2021Article
- Recent Advances in the Synthesis of Selenophenes and Their Derivatives.Molecules (Basel, Switzerland) · 2020Review
- Tetrasubstituted Selenophenes from the Stepwise Assembly of Molecular Fragments on a Diiron Frame and Final Cleavage of a Bridging Alkylidene.Inorganic chemistry · 2020Article
- Bromination of bis-(pyridin-2-yl) diselenide in methyl-ene chloride: the reaction mechanism and crystal structures of 1Acta crystallographica. Section E, Crystallographic communications · 2019Article
- Rational design and optimization of selenophenes with basic side chains as novel potent selective estrogen receptor modulators (SERMs) for breast cancer therapy.MedChemComm · 2017Article
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Authors and funding
11 authors at 4 institutions in 2 countries.
Funding
Abstract
The importance of the heterocyclic core elements with peripheral phenolic and alkyl substituents as a dominant structural motif of ligands for the estrogen receptor (ER) has been well recognized. In this study we expanded the structural diversity of core elements by preparing selenium-containing heterocycles and exploring the activities of these selenophenes on the two ERs, ERα and ERβ. Careful structure-activity relationship (SAR) analysis of their ER binding affinities showed that most selenophenes are ERβ-selective, with the position of the phenol substituents on the selenophene core and the nature of these substituents having a marked effect on their binding affinities. The compound bis(2-fluoro-4-hydroxyphenyl)selenophene (2 f) has the highest relative binding affinity (RBA) of 24.3 for ERβ. In transcription assays, most selenophenes were found to exhibit partial to full agonist activity for both ER subtypes, with compounds bis(2-methyl-4-hydroxyphenyl)selenophene (2 b), bis(4-fluoro-3-hydroxyphenyl)3-bromoselenophene (6 f), and 2,3,5-tris(hydroxyphenyl)thiophenes (8 b and 8 d) profiling as superagonists for ERα; however, several compounds display a range of ERα or ERβ antagonistic activities. A few selenophenes exhibited antiproliferative activity, with compound 8 c showing antiproliferative effects similar to that of 4-hydroxytamoxifen in breast cancer MCF-7 cells while being nontoxic to normal VERO cells. These new ligands could act as models for the development of novel agents leading to improved therapeutics that target the estrogen receptor.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.