Structure-activity relationship study of [1,2,3]thiadiazole necroptosis inhibitors

Bioorg Med Chem Lett. 2007 Dec 15;17(24):6836-40. doi: 10.1016/j.bmcl.2007.10.024. Epub 2007 Oct 17.

Abstract

Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling non-regulated necrosis. This form of cell death can be induced in an array of cell types in apoptotic deficient conditions with death receptor family ligands. A series of [1,2,3]thiadiazole benzylamides was found to be potent necroptosis inhibitors (called necrostatins). A structure-activity relationship study revealed that small cyclic alkyl groups (i.e. cyclopropyl) and 2,6-dihalobenzylamides at the 4- and 5-positions of the [1,2,3]thiadiazole, respectively, were optimal. In addition, when a small alkyl group (i.e. methyl) was present on the benzylic position all the necroptosis inhibitory activity resided with the (S)-enantiomer. Finally, replacement of the [1,2,3]thiadiazole with a variety of thiophene derivatives was tolerated, although some erosion of potency was observed.

Publication types

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

MeSH terms

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

Substances

  • Thiadiazoles
  • Tumor Necrosis Factor-alpha