Discovery of a Potent and Orally Bioavailable Zwitterionic Series of Selective Estrogen Receptor Degrader-Antagonists.


Journal

Journal of medicinal chemistry
ISSN: 1520-4804
Titre abrégé: J Med Chem
Pays: United States
ID NLM: 9716531

Informations de publication

Date de publication:
23 02 2023
Historique:
pubmed: 3 2 2023
medline: 25 2 2023
entrez: 2 2 2023
Statut: ppublish

Résumé

Herein, we report the optimization of a meta-substituted series of selective estrogen receptor degrader (SERD) antagonists for the treatment of ER+ breast cancer. Structure-based design together with the use of modeling and NMR to favor the bioactive conformation led to a highly potent series of basic SERDs with promising physicochemical properties. Issues with hERG activity resulted in a strategy of zwitterion formation and ultimately in the identification of

Identifiants

pubmed: 36727211
doi: 10.1021/acs.jmedchem.2c01964
doi:

Substances chimiques

Receptors, Estrogen 0
Selective Estrogen Receptor Modulators 0
Estrogen Antagonists 0
Estrogen Receptor alpha 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

2918-2945

Auteurs

James S Scott (JS)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Darren Stead (D)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Bernard Barlaam (B)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Jason Breed (J)

Discovery Sciences R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Rodrigo J Carbajo (RJ)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Elisabetta Chiarparin (E)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Natalie Cureton (N)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Paul R J Davey (PRJ)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

David I Fisher (DI)

Discovery Sciences R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Eric T Gangl (ET)

Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.

Tyler Grebe (T)

Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.

Ryan D Greenwood (RD)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Sudhir Hande (S)

Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.

Holia Hatoum-Mokdad (H)

Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.

Samantha J Hughes (SJ)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Thomas A Hunt (TA)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Tony Johnson (T)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Stefan L Kavanagh (SL)

Clinical Pharmacology and Safety Sciences, R&D, AstraZeneca, Cambridge CB2 OAA, United Kingdom.

Teresa C M Klinowska (TCM)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Carrie J B Larner (CJB)

Clinical Pharmacology and Safety Sciences, R&D, AstraZeneca, Cambridge CB2 OAA, United Kingdom.

Mandy Lawson (M)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Andrew S Lister (AS)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

David Longmire (D)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Stacey Marden (S)

Advanced Drug Delivery, Pharmaceutical Sciences, R&D, Boston, Massachusetts 02451, United States.

Thomas M McGuire (TM)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Caroline McMillan (C)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Lindsay McMurray (L)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Christopher J Morrow (CJ)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

J Willem M Nissink (JWM)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Thomas A Moss (TA)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Daniel H O'Donovan (DH)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Radoslaw Polanski (R)

Discovery Sciences R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Stephen Stokes (S)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Kumar Thakur (K)

Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.

Dawn Trueman (D)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Caroline Truman (C)

Discovery Sciences R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Michael J Tucker (MJ)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Haixia Wang (H)

Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.

Nicky Whalley (N)

Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.

Dedong Wu (D)

Advanced Drug Delivery, Pharmaceutical Sciences, R&D, Boston, Massachusetts 02451, United States.

Ye Wu (Y)

Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.

Bin Yang (B)

Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.

Wenzhan Yang (W)

Advanced Drug Delivery, Pharmaceutical Sciences, R&D, Boston, Massachusetts 02451, United States.

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Classifications MeSH