A New Chemotype of Chemically Tractable Nonsteroidal Estrogens Based on a Thieno[2,3-d]pyrimidine Co

Sammeta, Vamshikrishna Reddy; Norris, John D.; Artham, Sandeep; Torrice, Chad D.; Byemerwa, Jovita; Joiner, Carstyn; Fanning, Sean W.; McDonnell, Donald P.; Willson, Timothy M.

doi:10.1021/acsmedchemlett.2c00180

A New Chemotype of Chemically Tractable Nonsteroidal Estrogens Based on a Thieno[2,3-d]pyrimidine Co

Journal Article · 01 June 2022 · ACS Med. Chem. Lett.

DOI:https://doi.org/10.1021/acsmedchemlett.2c00180· OSTI ID:1900656

Sammeta, Vamshikrishna Reddy; Norris, John D.; Artham, Sandeep; Torrice, Chad D.; Byemerwa, Jovita; Joiner, Carstyn; Fanning, Sean W.; McDonnell, Donald P.; Willson, Timothy M.

Research Organization:: Advanced Photon Source (APS), Argonne National Laboratory (ANL), Argonne, IL (US)

Sponsoring Organization:: DOE - Office Of Science; DOD

OSTI ID:: 1900656

Journal Information:: ACS Med. Chem. Lett., Journal Name: ACS Med. Chem. Lett. Journal Issue: (7) Vol. 13

Country of Publication:: United States

Language:: ENGLISH

References (25)

Discovery of dual orexin receptor antagonists with rat sleep efficacy enabled by expansion of the acetonitrile-assisted/diphosgene-mediated 2,4-dichloropyrimidine synthesis Roecker, Anthony J.; Mercer, Swati P.; Harrell, C. Meacham Bioorganic & Medicinal Chemistry Letters, Vol. 24, Issue 9 https://doi.org/10.1016/j.bmcl.2014.03.052	journal	May 2014
Endocrine Modulators in the Food Chain and Environment Nilsson, Robert Toxicologic Pathology, Vol. 28, Issue 3 https://doi.org/10.1177/019262330002800311	journal	May 2000
Sources of estrogen and their importance Simpson, E. R. The Journal of Steroid Biochemistry and Molecular Biology, Vol. 86, Issue 3-5 https://doi.org/10.1016/S0960-0760(03)00360-1	journal	September 2003
An Efficient One-Pot Synthesis of Substituted 2-Aminothiophenes via Three-Component Gewald Reaction Catalyzed by l-Proline Wang, Tao; Huang, Xian-Gui; Liu, Jia Synlett, Vol. 2010, Issue 09 https://doi.org/10.1055/s-0029-1219917	journal	May 2010
Estrogen Receptors: How Do They Signal and What Are Their Targets Heldring, Nina; Pike, Ashley; Andersson, Sandra Physiological Reviews, Vol. 87, Issue 3 https://doi.org/10.1152/physrev.00026.2006	journal	July 2007
A facile and practical one-pot synthesis of multisubstituted 2-aminothiophenes via imidazole-catalyzed Gewald reaction Huang, Xian-Gui; Liu, Jia; Ren, Jiangmeng Tetrahedron, Vol. 67, Issue 34 https://doi.org/10.1016/j.tet.2011.06.061	journal	August 2011
The SERM/SERD bazedoxifene disrupts ESR1 helix 12 to overcome acquired hormone resistance in breast cancer cells Fanning, Sean W.; Jeselsohn, Rinath; Dharmarajan, Venkatasubramanian eLife, Vol. 7 https://doi.org/10.7554/eLife.37161	journal	November 2018
Phytoestrogens and Mycoestrogens Bind to the Rat Uterine Estrogen Receptor Branham, William S.; Dial, Stacey L.; Moland, Carrie L. The Journal of Nutrition, Vol. 132, Issue 4 https://doi.org/10.1093/jn/132.4.658	journal	April 2002
Antiestrogens and Selective Estrogen Receptor Modulators as Multifunctional Medicines. 1. Receptor Interactions Jordan, V. Craig Journal of Medicinal Chemistry, Vol. 46, Issue 6 https://doi.org/10.1021/jm020449y	journal	March 2003
Estrogen receptors and human disease Deroo, B. J. Journal of Clinical Investigation, Vol. 116, Issue 3 https://doi.org/10.1172/JCI27987	journal	March 2006
The History of DES, Lessons to be Learned Veurink, Marieke; Koster, Marlies; Berg, Lolkje T. W. de Jong-van den. Pharmacy World & Science, Vol. 27, Issue 3 https://doi.org/10.1007/s11096-005-3663-z	journal	June 2005
The 2010 Philip S. Portoghese Medicinal Chemistry Lectureship: Addressing the “Core Issue” in the Design of Estrogen Receptor Ligands: Award Address Katzenellenbogen, John A. Journal of Medicinal Chemistry, Vol. 54, Issue 15 https://doi.org/10.1021/jm200801h	journal	July 2011
Peptide Antagonists of the Human Estrogen Receptor Norris, J. D. Science, Vol. 285, Issue 5428 https://doi.org/10.1126/science.285.5428.744	journal	July 1999
Minireview: Estrogen Receptor-β: Mechanistic Insights from Recent Studies Deroo, Bonnie J.; Buensuceso, Adrian V. Molecular Endocrinology, Vol. 24, Issue 9 https://doi.org/10.1210/me.2009-0288	journal	September 2010
Discovery of potent thieno[2,3-d]pyrimidine VEGFR-2 inhibitors: Design, synthesis and enzyme inhibitory evaluation supported by molecular dynamics simulations Elrazaz, Eman Z.; Serya, Rabah A. T.; Ismail, Nasser S. M. Bioorganic Chemistry, Vol. 113 https://doi.org/10.1016/j.bioorg.2021.105019	journal	August 2021
The Gewald multicomponent reaction Huang, Yijun; Dömling, Alexander Molecular Diversity, Vol. 15, Issue 1 https://doi.org/10.1007/s11030-010-9229-6	journal	February 2010
Evaluation of ligand selectivity using reporter cell lines stably expressing estrogen receptor alpha or beta Escande, Aurélie; Pillon, Arnaud; Servant, Nadège Biochemical Pharmacology, Vol. 71, Issue 10 https://doi.org/10.1016/j.bcp.2006.02.002	journal	May 2006
Estrogen Receptors α and β as Determinants of Gene Expression: Influence of Ligand, Dose, and Chromatin Binding Chang, Edmund C.; Charn, Tze Howe; Park, Sung-Hee Molecular Endocrinology, Vol. 22, Issue 5 https://doi.org/10.1210/me.2007-0356	journal	May 2008
Estrogen receptor (ER) modulators each induce distinct conformational changes in ER and ER Paige, L. A.; Christensen, D. J.; Gron, H. Proceedings of the National Academy of Sciences, Vol. 96, Issue 7 https://doi.org/10.1073/pnas.96.7.3999	journal	March 1999
The History and Mechanism of Action of Fulvestrant Carlson, Robert W. Clinical Breast Cancer, Vol. 6 https://doi.org/10.3816/CBC.2005.s.008	journal	April 2005
Estrogen Receptor (ER)-β Reduces ERα-Regulated Gene Transcription, Supporting a “Ying Yang” Relationship between ERα and ERβ in Mice Lindberg, Marie K.; Movérare, Sofia; Skrtic, Stanko Molecular Endocrinology, Vol. 17, Issue 2 https://doi.org/10.1210/me.2002-0206	journal	February 2003
Oral Selective Estrogen Receptor Downregulators (SERDs), a Breakthrough Endocrine Therapy for Breast Cancer McDonnell, Donald P.; Wardell, Suzanne E.; Norris, John D. Journal of Medicinal Chemistry, Vol. 58, Issue 12 https://doi.org/10.1021/acs.jmedchem.5b00760	journal	March 2015
Acetonitrile-Mediated Synthesis of 2,4-Dichloroquinoline from 2-Ethynylaniline and 2,4-Dichloroquinazoline from Anthranilonitrile Lee, Jae Hak; Lee, Byoung Se; Shin, Hyunik Synlett, Issue 1 https://doi.org/10.1055/s-2005-922790	journal	January 2006
Medicinal Attributes of Thienopyrimidine Based Scaffold Targeting Tyrosine Kinases and Their Potential Anticancer Activities: Thienopyrimidine Based Scaffold Targeting Tyrosine Kinases Ghith, Amna; Ismail, Nasser S. M.; Youssef, Khairia Archiv der Pharmazie, Vol. 350, Issue 11 https://doi.org/10.1002/ardp.201700242	journal	October 2017
The Gewald Synthesis Sabnis, Ram W. Sulfur reports, Vol. 16, Issue 1 https://doi.org/10.1080/01961779408048964	journal	December 1994

Similar Records

A New Chemotype of Chemically Tractable Nonsteroidal Estrogens Based on a Thieno[2,3-d]pyrimidine Co

Journal Article · 2022 · ACS Med. Chem. Lett. · OSTI ID:1877195

Structural Determinants of the Binding and Activation of Estrogen Receptor α by Phenolic Thieno[2,3-d]pyrimidines

Journal Article · 2023 · Helvetica Chimica Acta · OSTI ID:2423644

Synthesis of substituted thieno(2,3-d)thiazoles and indolo(3,2-d)thiazoles

Journal Article · 1987 · Chem. Heterocycl. Compd. (Engl. Transl.); (United States) · OSTI ID:6893810

A New Chemotype of Chemically Tractable Nonsteroidal Estrogens Based on a Thieno[2,3-d]pyrimidine Co

Citation Formats

References (25)

Similar Records

Related Subjects