Discovery of benzofuran-3(2H)-one derivatives as novel DRAK2 inhibitors that protect islet β-cells from apoptosis

Eur J Med Chem. 2017 Apr 21:130:195-208. doi: 10.1016/j.ejmech.2017.02.048. Epub 2017 Feb 21.

Abstract

Death-associated protein kinase-related apoptosis-inducing kinase-2 (DRAK2) is a serine/threonine kinase that plays a key role in a wide variety of cell death signaling pathways. Inhibition of DRAK2 was found to efficiently protect islet β-cells from apoptosis and hence DRAK2 inhibitors represent a promising therapeutic strategy for the treatment of diabetes. Only very few chemical entities targeting DRAK2 are currently known. We carried out a high throughput screening and identified compound 4 as a moderate DRAK2 inhibitor with an IC50 value of 3.15 μM. Subsequent SAR studies of hit compound 4 led to the development of novel benzofuran-3(2H)-one series of DRAK2 inhibitors with improved potency and favorable selectivity profiles against 26 selected kinases. Importantly, most potent compounds 40 (IC50 = 0.33 μM) and 41 (IC50 = 0.25 μM) were found to protect islet β-cells from apoptosis in dose-dependent manners. These data support the notion that small molecule inhibitors of DRAK2 represents a promising strategy for the treatment of diabetes.

Keywords: Apoptosis; DRAK2 inhibitor; Diabetes; Islet β-cell protection.

MeSH terms

  • Apoptosis / drug effects*
  • Apoptosis Regulatory Proteins / antagonists & inhibitors*
  • B-Lymphocytes / cytology*
  • Benzofurans / chemistry
  • Benzofurans / pharmacology*
  • Cells, Cultured
  • Diabetes Mellitus / drug therapy
  • Drug Discovery
  • Humans
  • Inhibitory Concentration 50
  • Islets of Langerhans / cytology*
  • Protective Agents / chemistry
  • Protective Agents / pharmacology
  • Protein Serine-Threonine Kinases / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • Apoptosis Regulatory Proteins
  • Benzofurans
  • Protective Agents
  • Protein Serine-Threonine Kinases
  • STK17B protein, human