Synthesis and structure-activity relationships for some novel diflapolin derivatives with benzimidazole subunit

J Enzyme Inhib Med Chem. 2022 Dec;37(1):1752-1764. doi: 10.1080/14756366.2022.2087645.

Abstract

A series of derivatives of the potent dual soluble epoxide hydrolase (sEH)/5-lipoxygenase-activating protein (FLAP) inhibitor diflapolin was designed, synthesised, and characterised. These novel compounds, which contain a benzimidazole subunit were evaluated for their inhibitory activity against sEH and FLAP. Molecular modelling tools were applied to analyse structure-activity relationships (SAR) on both targets and to predict solubility and gastrointestinal (GI) absorption. The most promising dual inhibitors of these series are 5a, 6b, and 6c.

Keywords: 5-lipoxygenase activating protein (FLAP); Diflapolin; benzimidazoles; solubility and GI absorption prediction; soluble epoxide hydrolase (sEH).

MeSH terms

  • 5-Lipoxygenase-Activating Proteins / metabolism
  • Benzimidazoles* / pharmacology
  • Enzyme Inhibitors / pharmacology
  • Epoxide Hydrolases*
  • Lipoxygenase Inhibitors / pharmacology
  • Structure-Activity Relationship

Substances

  • 5-Lipoxygenase-Activating Proteins
  • Benzimidazoles
  • Enzyme Inhibitors
  • Lipoxygenase Inhibitors
  • Epoxide Hydrolases