ArticleJournal of medicinal chemistry2013
Thiophene-core estrogen receptor ligands having superagonist activity.
Article in Journal of medicinal chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 57 citations in OpenAlex.
- Article
- Evolution of a Strategy for the Total Synthesis of (+)-Cornexistin.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.Topics in current chemistry (Cham) · 2021Review
- Article
- Rational design and optimization of selenophenes with basic side chains as novel potent selective estrogen receptor modulators (SERMs) for breast cancer therapy.MedChemComm · 2017Article
- Selenophenes: Introducing a New Element into the Core of Non-Steroidal Estrogen Receptor Ligands.ChemMedChem · 2017Article
- Site-selective Suzuki-Miyaura coupling of heteroaryl halides - understanding the trends for pharmaceutically important classes.Chemical science · 2017Article
- Selenophene and thiophene-core estrogen receptor ligands that inhibit motility and development of parasitic stages of Haemonchus contortus.Parasites & vectors · 2016Article
- Predictive features of ligand-specific signaling through the estrogen receptor.Molecular systems biology · 2016Article
- Selective Human Estrogen Receptor Partial Agonists (ShERPAs) for Tamoxifen-Resistant Breast Cancer.Journal of medicinal chemistry · 2016Article
- Synthesis and receptor binding in trans-CD ring-fused A-CD estrogens: comparison with the cis-fused isomers.Bioorganic & medicinal chemistry letters · 2014Article
- Triaryl-substituted Schiff bases are high-affinity subtype-selective ligands for the estrogen receptor.Journal of medicinal chemistry · 2014Article
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Authors and funding
10 authors at 4 institutions in 2 countries.
Funding
Abstract
To probe the importance of the heterocyclic core of estrogen receptor (ER) ligands, we prepared a series of thiophene-core ligands by Suzuki cross-coupling of aryl boronic acids with bromo-thiophenes and we assessed their receptor binding and cell biological activities. The disposition of the phenol substituents on the thiophene core, at alternate or adjacent sites, and the nature of substituents on these phenols, all contribute to binding affinity and subtype selectivity. Most of the bis(hydroxyphenyl)-thiophenes were ERβ selective, whereas the tris(hydroxyphenyl)-thiophenes were ERα selective; analogous furan-core compounds generally have lower affinity and less selectivity. Some diarylthiophenes show distinct superagonist activity in reporter gene assays, giving maximal activities 2-3 times that of estradiol, and modeling suggests that these ligands have a different interaction with a hydrogen-bonding residue in helix-11. Ligand-core modification may be a new strategy for developing ER ligands whose selectivity is based on having transcriptional activity greater than that of estradiol.
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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.