Design, synthesis, and structure-activity relationship (SAR) of N-[7-(4-hydroxyphenoxy)-6-methylindan-4-yl]malonamic acids as thyroid hormone receptor β (TRβ) selective agonists

Bioorg Med Chem. 2013 Feb 1;21(3):592-607. doi: 10.1016/j.bmc.2012.12.002. Epub 2012 Dec 11.

Abstract

Highly TRβ selective thyromimetics have several potential therapeutic applications. Based on the novel indane derivative KTA-439 with high receptor (TRβ) and organ (liver) selectivity, a series of thyroid hormone analogues were prepared, in which the isopropyl at the 3'-position was replaced with alkyl and aralkyl moieties of variable lengths and branches. Binding assays for these human TRs and reporter cell assays showed that 2-arylethyl derivatives had higher TRβ selectivity than KTA-439. KTA-574, a representative 2-arylethyl derivative, had TRβ specificity in a binding assay and exhibited full agonism in a reporter cell assay.

MeSH terms

  • Dose-Response Relationship, Drug
  • Drug Design*
  • Humans
  • Malonates / chemical synthesis
  • Malonates / chemistry
  • Malonates / pharmacology*
  • Models, Molecular
  • Molecular Structure
  • Structure-Activity Relationship
  • Thyroid Hormone Receptors beta / agonists*

Substances

  • Malonates
  • Thyroid Hormone Receptors beta
  • malonamic acid