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

ABSTRACT: Despite continued interest in the development of nonsteroidal estrogens and antiestrogens, there are only a few chemotypes of estrogen receptor ligands. Using targeted screening in a ligand sensing assay, we identified a phenolic thieno[2,3-d]pyrimidine with affinity for estrogen receptor α. An efficient three-step synthesis of the heterocyclic core and structure-guided optimization of the substituents resulted in a series of potent nonsteroidal estrogens. The chemical tractability of the thieno[2,3-d]pyrimidine chemotype will support the design of new estrogen receptor ligands as therapeutic hormones and antihormones.

SUBMITTER: Sammeta VR 

PROVIDER: S-EPMC9290010 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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A New Chemotype of Chemically Tractable Nonsteroidal Estrogens Based on a Thieno[2,3-<i>d</i>]pyrimidine Core.

Sammeta Vamshikrishna Reddy VR   Norris John D JD   Artham Sandeep S   Torrice Chad D CD   Byemerwa Jovita J   Joiner Carstyn C   Fanning Sean W SW   McDonnell Donald P DP   Willson Timothy M TM  

ACS medicinal chemistry letters 20220610 7

Despite continued interest in the development of nonsteroidal estrogens and antiestrogens, there are only a few chemotypes of estrogen receptor ligands. Using targeted screening in a ligand sensing assay, we identified a phenolic thieno[2,3-<i>d</i>]pyrimidine with affinity for estrogen receptor α. An efficient three-step synthesis of the heterocyclic core and structure-guided optimization of the substituents resulted in a series of potent nonsteroidal estrogens. The chemical tractability of the  ...[more]

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