N-(7-Cyano-6-(4-fluoro-3-(2-(3-(trifluoromethyl)phenyl)acetamido)phenoxy)benzo[ d]thiazol-2-yl)cyclopropanecarboxamide (TAK-632) Analogues as Novel Necroptosis Inhibitors by Targeting Receptor-Interacting Protein Kinase 3 (RIPK3): Synthesis, Structure-Activity Relationships, and in Vivo Efficacy

J Med Chem. 2019 Jul 25;62(14):6665-6681. doi: 10.1021/acs.jmedchem.9b00611. Epub 2019 May 28.

Abstract

Necroptosis, a form of programmed cell death, plays a critical role in various diseases, including inflammatory, infectious, and degenerative diseases. We previously identified N-(7-cyano-6-(4-fluoro-3-(2-(3-(trifluoromethyl)phenyl)acetamido)phenoxy)benzo[d]thiazol-2-yl)cyclopropanecarboxamide (TAK-632) (6) as a potent inhibitor of necroptosis by targeting both receptor-interacting protein kinase 1 (RIPK1) and 3 (RIPK3) kinases. Herein, we performed three rounds of structural optimizations of TAK-632 and elucidated structure-activity relationships to generate more potent inhibitors by targeting RIPK3. The analogues with carbamide groups exhibited great antinecroptotic activities, and compound 42 showed >60-fold selectivity for RIPK3 than RIPK1. It blocked necrosome formation by specifically inhibiting the phosphorylation of RIPK3 in necroptotic cells. In a tumor necrosis factor-induced systemic inflammatory response syndrome model, it significantly protected mice from hypothermia and death at a dose of 5 mg/kg, which was much more effective than TAK-632. Moreover, it showed favorable and druglike pharmacokinetic properties in rats with an oral bioavailability of 25.2%. Thus, these RIPK3-targeting small molecules represent promising lead structures for further development.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry
  • Amides / pharmacokinetics
  • Amides / pharmacology
  • Animals
  • Benzothiazoles / chemical synthesis
  • Benzothiazoles / chemistry*
  • Benzothiazoles / pharmacokinetics
  • Benzothiazoles / pharmacology*
  • Cyclopropanes / chemical synthesis
  • Cyclopropanes / chemistry
  • Cyclopropanes / pharmacokinetics
  • Cyclopropanes / pharmacology
  • Female
  • HT29 Cells
  • Halogenation
  • Humans
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Molecular Docking Simulation
  • Necroptosis / drug effects*
  • Nitriles / chemical synthesis
  • Nitriles / chemistry*
  • Nitriles / pharmacokinetics
  • Nitriles / pharmacology*
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / pharmacokinetics
  • Protein Kinase Inhibitors / pharmacology*
  • Rats, Sprague-Dawley
  • Receptor-Interacting Protein Serine-Threonine Kinases / antagonists & inhibitors*
  • Receptor-Interacting Protein Serine-Threonine Kinases / metabolism
  • Structure-Activity Relationship

Substances

  • Amides
  • Benzothiazoles
  • Cyclopropanes
  • Nitriles
  • Protein Kinase Inhibitors
  • TAK-632
  • RIPK3 protein, human
  • Receptor-Interacting Protein Serine-Threonine Kinases
  • cyclopropanecarboxamide