Structure-activity relationship and liver microsome stability studies of pyrrole necroptosis inhibitors

Bioorg Med Chem Lett. 2008 Jun 1;18(11):3219-23. doi: 10.1016/j.bmcl.2008.04.048. Epub 2008 Apr 25.

Abstract

Necroptosis is a regulated caspase-independent cell death pathway resulting in morphology reminiscent of passive non-regulated necrosis. Several diverse structure classes of necroptosis inhibitors have been reported to date, including a series of [1,2,3]thiadiazole benzylamide derivatives. However, initial evaluation of mouse liver microsome stability indicated that this series of compounds was rapidly degraded. A structure-activity relationship (SAR) study of the [1,2,3]thiadiazole benzylamide series revealed that increased mouse liver microsome stability and increased necroptosis inhibitory activity could be accomplished by replacement of the 4-cyclopropyl-[1,2,3]thiadiazole with a 5-cyano-1-methylpyrrole. In addition, the SAR and the cellular activity profiles, utilizing different cell types and necroptosis-inducing stimuli, of representative [1,2,3]thiadiazole and pyrrole derivatives were very similar suggesting that the two compound series inhibit necroptosis in the same manner.

Publication types

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

MeSH terms

  • Apoptosis / drug effects*
  • Humans
  • Jurkat Cells
  • Microsomes, Liver / drug effects
  • Molecular Structure
  • Necrosis / drug therapy
  • Necrosis / pathology
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry*
  • Pyrroles / pharmacology*
  • Structure-Activity Relationship
  • Tumor Necrosis Factor-alpha / pharmacology

Substances

  • Pyrroles
  • Tumor Necrosis Factor-alpha