Structure-activity relationship study of novel necroptosis inhibitors

Bioorg Med Chem Lett. 2005 Nov 15;15(22):5039-44. doi: 10.1016/j.bmcl.2005.07.077.

Abstract

Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-alpha. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration.

Publication types

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

MeSH terms

  • Animals
  • Cell Death / drug effects
  • Humans
  • Hydantoins / administration & dosage
  • Hydantoins / chemical synthesis
  • Hydantoins / chemistry*
  • Hydantoins / pharmacology*
  • Injections, Intravenous
  • Jurkat Cells
  • Male
  • Methylation
  • Mice
  • Molecular Structure
  • Necrosis
  • Structure-Activity Relationship
  • Sulfhydryl Compounds / chemistry*
  • Tumor Necrosis Factor-alpha / pharmacology

Substances

  • Hydantoins
  • Sulfhydryl Compounds
  • Tumor Necrosis Factor-alpha