An efficient substitution reaction for the preparation of thyroid hormone analogues

Hikari A I Yoshihara, Grazia Chiellini, Timothy J. Mitchison, Thomas (Tom) Scanlan

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

The substitution of the sterically hindered carbon of the potent thyroid hormone agonist, GC-1, was effected by a reaction based on the solvolysis of the benzylic hydroxyl group. The reaction was found to proceed in high yield with a variety of nucleophiles including alcohols, thiols, allyl silanes and electron-rich aromatic compounds, providing a convenient route to the synthesis of new thyroid hormone analogues. Copyright (C) 1998 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)1179-1183
Number of pages5
JournalBioorganic and Medicinal Chemistry
Volume6
Issue number8
DOIs
Publication statusPublished - Aug 1998
Externally publishedYes

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Keywords

  • S(N)1
  • Thyroid hormone
  • Thyromimetic

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

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