Discovery of 7-azaindole derivatives as potent Orai inhibitors showing efficacy in a preclinical model of asthma

Bioorg Med Chem Lett. 2015 Mar 15;25(6):1217-22. doi: 10.1016/j.bmcl.2015.01.063. Epub 2015 Feb 4.

Abstract

Synthesis and SAR of a series of 7-azaindoles as Orai channel inhibitors showing good potency inhibiting IL-2 production in Jurkat cells is described. Compound 14d displaying best pharmacokinetic properties was further characterized in a model of allergen induced asthma showing inhibition in the number of eosinophils in BALF. High lipophilicity remains as one of the main challenges for this class of compounds.

Keywords: CRAC channel; IL-2 inhibitors; LAD2; OVA model; Orai inhibitors.

MeSH terms

  • Animals
  • Asthma
  • Aza Compounds / chemistry
  • Calcium Channel Blockers / chemistry*
  • Calcium Channel Blockers / pharmacokinetics
  • Calcium Channel Blockers / therapeutic use
  • Calcium Channels / chemistry*
  • Calcium Channels / metabolism
  • Disease Models, Animal
  • Drug Evaluation, Preclinical
  • Half-Life
  • Humans
  • Hypersensitivity / drug therapy
  • Hypersensitivity / immunology
  • Indoles / chemistry*
  • Indoles / pharmacokinetics
  • Indoles / therapeutic use
  • Interleukin-2 / blood
  • Interleukin-2 / metabolism
  • Jurkat Cells
  • Microsomes / metabolism
  • Models, Biological
  • Ovalbumin / immunology
  • Protein Binding
  • Pyridines / chemistry*
  • Pyridines / pharmacokinetics
  • Pyridines / therapeutic use
  • Pyrroles / chemistry*
  • Pyrroles / pharmacokinetics
  • Pyrroles / therapeutic use
  • Rats
  • Structure-Activity Relationship

Substances

  • Aza Compounds
  • Calcium Channel Blockers
  • Calcium Channels
  • Indoles
  • Interleukin-2
  • Pyridines
  • Pyrroles
  • Ovalbumin