3-(7-Azaindolyl)-4-indolylmaleimides as a novel class of mutant isocitrate dehydrogenase-1 inhibitors: Design, synthesis, and biological evaluation

Arch Pharm (Weinheim). 2018 Oct;351(10):e1800039. doi: 10.1002/ardp.201800039. Epub 2018 Aug 16.

Abstract

A series of 3-(7-azainodyl)-4-indolylmaleimides was designed, synthesized, and evaluated for their isocitrate dehydrogenase 1 (IDH1)/R132H inhibitory activities. Many compounds such as 11a, 11c, 11e, 11g, and 11s exhibited favorable inhibitory effects on IDH1/R132H and were highly selective against the wild-type IDH1. Evaluation of the biological activities at the cellular level showed that compounds 11a, 11c, 11e, 11g, and 11s could effectively suppress the production of 2-hydroxyglutaric acid in U87MG cells expressing IDH1/R132H. Preliminary structure-activity relationship (SAR) and molecular modeling studies were discussed based on the experimental data obtained. These findings may provide new insights into the development of novel IDH1/R132H inhibitors.

Keywords: 2-hydroxyglutaric acid; 3-(7-azaindoyl)-4-indolylmaleimides; isocitrate dehydrogenase 1 inhibitors; tumor.

MeSH terms

  • Dose-Response Relationship, Drug
  • Drug Design*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Indoles / chemical synthesis
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Isocitrate Dehydrogenase / antagonists & inhibitors*
  • Isocitrate Dehydrogenase / genetics
  • Isocitrate Dehydrogenase / metabolism
  • Maleimides / chemical synthesis
  • Maleimides / chemistry
  • Maleimides / pharmacology*
  • Models, Molecular
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • 3-(7-azaindolyl)-4-indolylmaleimides
  • Enzyme Inhibitors
  • Indoles
  • Maleimides
  • Isocitrate Dehydrogenase