Discovery of an Acrylic Acid Based Tetrahydroisoquinoline as an Orally Bioavailable Selective Estrogen Receptor Degrader for ERα+ Breast Cancer

J Med Chem. 2017 Apr 13;60(7):2790-2818. doi: 10.1021/acs.jmedchem.6b01468. Epub 2017 Mar 15.

Abstract

Tetrahydroisoquinoline 40 has been identified as a potent ERα antagonist and selective estrogen receptor degrader (SERD), exhibiting good oral bioavailability, antitumor efficacy, and SERD activity in vivo. We outline the discovery and chemical optimization of the THIQ scaffold leading to THIQ 40 and showcase the racemization of the scaffold, pharmacokinetic studies in preclinical species, and the in vivo efficacy of THIQ 40 in a MCF-7 human breast cancer xenograft model.

Publication types

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

MeSH terms

  • Acrylates / chemistry
  • Acrylates / pharmacokinetics
  • Acrylates / pharmacology
  • Acrylates / therapeutic use
  • Administration, Oral
  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology
  • Antineoplastic Agents / therapeutic use*
  • Breast / drug effects*
  • Breast / metabolism
  • Breast / pathology
  • Breast Neoplasms / drug therapy*
  • Breast Neoplasms / metabolism
  • Breast Neoplasms / pathology
  • Dogs
  • Drug Discovery
  • Estrogen Receptor alpha / antagonists & inhibitors*
  • Estrogen Receptor alpha / metabolism
  • Female
  • Humans
  • MCF-7 Cells
  • Mice, Inbred C57BL
  • Molecular Docking Simulation
  • Proteolysis / drug effects
  • Tetrahydroisoquinolines / chemistry*
  • Tetrahydroisoquinolines / pharmacokinetics
  • Tetrahydroisoquinolines / pharmacology
  • Tetrahydroisoquinolines / therapeutic use*

Substances

  • Acrylates
  • Antineoplastic Agents
  • Estrogen Receptor alpha
  • Tetrahydroisoquinolines
  • acrylic acid