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Estrogen receptor ligands. Part 9: Dihydrobenzoxathiin SERAMs with alkyl substituted pyrrolidine side chains and linkers.

Blizzard TA, Dininno F, Morgan JD, Chen HY, Wu JY, Kim S, Chan W, Birzin ET, Yang YT, Pai LY, Fitzgerald PM, Sharma N, Li Y, Zhang Z, Hayes EC, Dasilva CA, Tang W, Rohrer SP, Schaeffer JM, Hammond ML
Bioorg Med Chem Lett 15 107-13 (2005)
Related entries: 1xp6, 1xp9, 1xpc

Cited: 39 times
EuropePMC logo PMID: 15582421

Abstract

A series of dihydrobenzoxathiin SERAMs with alkylated pyrrolidine side chains or alkylated linkers was prepared. Minor modifications in the side chain or linker resulted in significant effects on biological activity, especially in uterine tissue.

Reviews - 1xp1 mentioned but not cited (1)

  1. Versatility or promiscuity: the estrogen receptors, control of ligand selectivity and an update on subtype selective ligands. Ng HW, Perkins R, Tong W, Hong H. Int J Environ Res Public Health 11 8709-8742 (2014)

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  2. The 2.0 A crystal structure of the ERalpha ligand-binding domain complexed with lasofoxifene. Vajdos FF, Hoth LR, Geoghegan KF, Simons SP, LeMotte PK, Danley DE, Ammirati MJ, Pandit J. Protein Sci 16 897-905 (2007)
  3. Training a scoring function for the alignment of small molecules. Chan SL, Labute P. J Chem Inf Model 50 1724-1735 (2010)
  4. Integration of ligand-based drug screening with structure-based drug screening by combining maximum volume overlapping score with ligand docking. Fukunishi Y, Nakamura H. Pharmaceuticals (Basel) 5 1332-1345 (2012)
  5. Virtual screening of potentially endocrine-disrupting chemicals against nuclear receptors and its application to identify PPARγ-bound fatty acids. Jaladanki CK, He Y, Zhao LN, Maurer-Stroh S, Loo LH, Song H, Fan H. Arch Toxicol 95 355-374 (2021)
  6. Characterization of ligand type of estrogen receptor by MD simulation and mm-PBSA free energy analysis. Liu JY, Mooney SD. Int J Biochem Mol Biol 2 190-198 (2011)
  7. Network Pharmacology-Based Analysis on the Action Mechanism of Oleanolic Acid to Alleviate Osteoporosis. Wu Y, Gao LJ, Fan YS, Chen Y, Li Q. ACS Omega 6 28410-28420 (2021)
  8. Docking study of triphenylphosphonium cations as estrogen receptor alpha modulators. Salisbury JP, Williams JC. Bioinformation 3 303-307 (2009)
  9. Human Estrogen Receptor Alpha Antagonists, Part 3: 3-D Pharmacophore and 3-D QSAR Guided Brefeldin A Hit-to-Lead Optimization toward New Breast Cancer Suppressants. Kurtanović N, Tomašević N, Matić S, Proia E, Sabatino M, Antonini L, Mladenović M, Ragno R. Molecules 27 2823 (2022)
  10. Predicting Potential Endocrine Disrupting Chemicals Binding to Estrogen Receptor α (ERα) Using a Pipeline Combining Structure-Based and Ligand-Based in Silico Methods. Sellami A, Montes M, Lagarde N. Int J Mol Sci 22 2846 (2021)


Reviews citing this publication (4)

  1. Estrogen receptors: how do they signal and what are their targets. Heldring N, Pike A, Andersson S, Matthews J, Cheng G, Hartman J, Tujague M, Ström A, Treuter E, Warner M, Gustafsson JA. Physiol Rev 87 905-931 (2007)
  2. Structure-function relationship of estrogen receptor alpha and beta: impact on human health. Ascenzi P, Bocedi A, Marino M. Mol Aspects Med 27 299-402 (2006)
  3. Lessons learnt from structural studies of the oestrogen receptor. Pike AC. Best Pract Res Clin Endocrinol Metab 20 1-14 (2006)
  4. Estrogen Receptor-α Targeting: PROTACs, SNIPERs, Peptide-PROTACs, Antibody Conjugated PROTACs and SNIPERs. Negi A, Kesari KK, Voisin-Chiret AS. Pharmaceutics 14 2523 (2022)

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  2. Mechanisms of Nickel-Catalyzed Coupling Reactions and Applications in Alkene Functionalization. Diccianni J, Lin Q, Diao T. Acc Chem Res 53 906-919 (2020)
  3. Pharmacophore modeling using site-identification by ligand competitive saturation (SILCS) with multiple probe molecules. Yu W, Lakkaraju SK, Raman EP, Fang L, MacKerell AD. J Chem Inf Model 55 407-420 (2015)
  4. Competitive molecular docking approach for predicting estrogen receptor subtype α agonists and antagonists. Ng HW, Zhang W, Shu M, Luo H, Ge W, Perkins R, Tong W, Hong H. BMC Bioinformatics 15 Suppl 11 S4 (2014)
  5. Estrogen receptor ligands. Part 10: Chromanes: old scaffolds for new SERAMs. Tan Q, Blizzard TA, Morgan JD, Birzin ET, Chan W, Yang YT, Pai LY, Hayes EC, DaSilva CA, Warrier S, Yudkovitz J, Wilkinson HA, Sharma N, Fitzgerald PM, Li S, Colwell L, Fisher JE, Adamski S, Reszka AA, Kimmel D, DiNinno F, Rohrer SP, Freedman LP, Schaeffer JM, Hammond ML. Bioorg Med Chem Lett 15 1675-1681 (2005)
  6. Androstenediol analogs as ER-beta-selective SERMs. Blizzard TA, Gude C, Morgan JD, Chan W, Birzin ET, Mojena M, Tudela C, Chen F, Knecht K, Su Q, Kraker B, Mosley RT, Holmes MA, Sharma N, Fitzgerald PM, Rohrer SP, Hammond ML. Bioorg Med Chem Lett 16 834-838 (2006)
  7. Distinct mechanisms of endocrine disruption of DDT-related pesticides toward estrogen receptor α and estrogen-related receptor γ. Zhuang S, Zhang J, Wen Y, Zhang C, Liu W. Environ Toxicol Chem 31 2597-2605 (2012)
  8. Estrogen receptor ligands. Part 16: 2-Aryl indoles as highly subtype selective ligands for ERalpha. Dykstra KD, Guo L, Birzin ET, Chan W, Yang YT, Hayes EC, DaSilva CA, Pai LY, Mosley RT, Kraker B, Fitzgerald PM, DiNinno F, Rohrer SP, Schaeffer JM, Hammond ML. Bioorg Med Chem Lett 17 2322-2328 (2007)
  9. Pharmacophore and QSAR modeling of estrogen receptor beta ligands and subsequent validation and in silico search for new hits. Taha MO, Tarairah M, Zalloum H, Abu-Sheikha G. J Mol Graph Model 28 383-400 (2010)
  10. Structural and chemical basis for enhanced affinity and potency for a large series of estrogen receptor ligands: 2D and 3D QSAR studies. Salum Lde B, Polikarpov I, Andricopulo AD. J Mol Graph Model 26 434-442 (2007)
  11. Identification of xenoestrogens in food additives by an integrated in silico and in vitro approach. Amadasi A, Mozzarelli A, Meda C, Maggi A, Cozzini P. Chem Res Toxicol 22 52-63 (2009)
  12. Estrogen receptor ligands. Part 13: Dihydrobenzoxathiin SERAMs with an optimized antagonist side chain. Blizzard TA, DiNinno F, Chen HY, Kim S, Wu JY, Chan W, Birzin ET, Yang YT, Pai LY, Hayes EC, DaSilva CA, Rohrer SP, Schaeffer JM, Hammond ML. Bioorg Med Chem Lett 15 3912-3916 (2005)
  13. Molecular insights on xenoestrogenic potential of zearalenone-14-glucoside through a mixed in vitro/in silico approach. Dellafiora L, Ruotolo R, Perotti A, Cirlini M, Galaverna G, Cozzini P, Buschini A, Dall'Asta C. Food Chem Toxicol 108 257-266 (2017)
  14. Metal-free O-H/C-H difunctionalization of phenols by o-hydroxyarylsulfonium salts in water. Chen D, Feng Q, Yang Y, Cai XM, Wang F, Huang S. Chem Sci 8 1601-1606 (2017)
  15. Novel Promising Estrogenic Receptor Modulators: Cytotoxic and Estrogenic Activity of Benzanilides and Dithiobenzanilides. Kucinska M, Giron MD, Piotrowska H, Lisiak N, Granig WH, Lopez-Jaramillo FJ, Salto R, Murias M, Erker T. PLoS One 11 e0145615 (2016)
  16. Structure-Based Understanding of Binding Affinity and Mode of Estrogen Receptor α Agonists and Antagonists. Lee S, Barron MG. PLoS One 12 e0169607 (2017)
  17. Bridged androstenediol analogs as ER-beta selective SERMs. Blizzard TA, Gude C, Chan W, Birzin ET, Mojena M, Tudela C, Chen F, Knecht K, Su Q, Kraker B, Holmes MA, Rohrer SP, Hammond ML. Bioorg Med Chem Lett 17 2944-2948 (2007)
  18. Prediction of binding affinity for estrogen receptor alpha modulators using statistical learning approaches. Wang Y, Li Y, Ding J, Wang Y, Chang Y. Mol Divers 12 93-102 (2008)
  19. Estrogen receptor ligands. Part 14: application of novel antagonist side chains to existing platforms. Blizzard TA, Morgan JD, Chan W, Birzin ET, Pai LY, Hayes EC, DaSilva CA, Mosley RT, Yang YT, Rohrer SP, Dininno F, Hammond ML. Bioorg Med Chem Lett 15 5124-5128 (2005)
  20. Structural analysis of estrogen receptors: interaction between estrogen receptors and cav-1 within the caveolae†. Pastore MB, Landeros RV, Chen DB, Magness RR. Biol Reprod 100 495-504 (2019)
  21. Discovery of novel natural compound inhibitors targeting estrogen receptor α by an integrated virtual screening strategy. Yu E, Xu Y, Shi Y, Yu Q, Liu J, Xu L. J Mol Model 25 278 (2019)
  22. Flexi-pharma: a molecule-ranking strategy for virtual screening using pharmacophores from ligand-free conformational ensembles. Lans I, Palacio-Rodríguez K, Cavasotto CN, Cossio P. J Comput Aided Mol Des 34 1063-1077 (2020)
  23. Sdfconf: A Novel, Flexible, and Robust Molecular Data Management Tool. Lätti ST, Niinivehmas S, Pentikäinen OT. J Chem Inf Model 62 9-15 (2022)
  24. ER/AR Multi-Conformational Docking Server: A Tool for Discovering and Studying Estrogen and Androgen Receptor Modulators. Wang F, Hu S, Ma DQ, Li Q, Li HC, Liang JY, Chang S, Kong R. Front Pharmacol 13 800885 (2022)


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