Beware of N-Benzoyloxybenzamides

Molecules. 2024 Oct 31;29(21):5143. doi: 10.3390/molecules29215143.

Abstract

Following a High-Throughput Screening campaign to discover inhibitors of acid ceramidase, we report the novel and extremely potent covalent inhibitor, 1. Following resynthesis and stability monitoring, we discovered that 1 is chemically unstable and reacts with DMSO at room temperature. This mode of decomposition is likely general for this class of compound, and we urge caution for their use in drug discovery research.

Keywords: N-benzoyloxybenzamides; PAINS; acid ceramidase.

MeSH terms

  • Acid Ceramidase / antagonists & inhibitors
  • Acid Ceramidase / metabolism
  • Benzamides* / chemistry
  • Benzamides* / pharmacology
  • Dimethyl Sulfoxide / chemistry
  • Drug Discovery
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • High-Throughput Screening Assays
  • Humans
  • Molecular Structure

Substances

  • Benzamides
  • Acid Ceramidase
  • Enzyme Inhibitors
  • Dimethyl Sulfoxide

Grants and funding

This research has been, in part, funded by the Coleg Cymraeg Cenedlaethol and the Harrington Rare Disease Scholar Award.