New synthetic routes to thyroid hormone analogs: d6-sobetirome, 3H-sobetirome, and the antagonist NH-3

Andrew T. Placzek, Thomas S. Scanlan

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

Abstract New synthetic routes for the preparation of isotopically labeled versions of thyroid hormone agonist sobetirome were developed using Knochel's iodine-magnesium exchange. A more efficient synthesis of the thyroid hormone antagonist NH-3 was developed from a common intermediate in the sobetirome route. Using the new synthetic routes, d6-and 3H-sobetirome were prepared for their use in studying biodistribution and the cellular uptake of sobetirome. The new route to NH-3 allows for a more rapid and efficient synthesis and provides access to an advanced intermediate to facilitate antagonist analog production in the final bond-forming synthetic step.

Original languageEnglish (US)
Article number26767
Pages (from-to)5946-5951
Number of pages6
JournalTetrahedron
Volume71
Issue number35
DOIs
StatePublished - Jul 25 2015

Keywords

  • NH-3
  • Sobetirome
  • Thyroid hormone
  • Thyromimetics

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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