New synthetic routes to thyroid hormone analogs

d6-sobetirome, 3H-sobetirome, and the antagonist NH-3

Andrew T. Placzek, Thomas (Tom) Scanlan

Research output: Contribution to journalArticle

11 Citations (Scopus)

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 - Mar 23 2015

Fingerprint

Thyroid Hormones
Hormone Antagonists
Antithyroid Agents
Iodine
Magnesium
Ion exchange
GC 1 compound

Keywords

  • NH-3
  • Sobetirome
  • Thyroid hormone
  • Thyromimetics

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

New synthetic routes to thyroid hormone analogs : d6-sobetirome, 3H-sobetirome, and the antagonist NH-3. / Placzek, Andrew T.; Scanlan, Thomas (Tom).

In: Tetrahedron, Vol. 71, No. 35, 26767, 23.03.2015, p. 5946-5951.

Research output: Contribution to journalArticle

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