An efficient substitution reaction for the preparation of thyroid hormone analogues

Bioorg Med Chem. 1998 Aug;6(8):1179-83. doi: 10.1016/s0968-0896(98)00085-6.

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Benzophenones / chemical synthesis*
  • Benzophenones / chemistry
  • Ligands
  • Receptors, Thyroid Hormone / antagonists & inhibitors*
  • Thyroid Hormones / chemical synthesis*
  • Thyroid Hormones / chemistry
  • Triiodothyronine / analogs & derivatives
  • Triiodothyronine / chemical synthesis
  • Triiodothyronine / chemistry

Substances

  • Benzophenones
  • Ligands
  • Receptors, Thyroid Hormone
  • Thyroid Hormones
  • Triiodothyronine