Novel potent and selective calcium-release-activated calcium (CRAC) channel inhibitors. Part 2: Synthesis and inhibitory activity of aryl-3-trifluoromethylpyrazoles

Bioorg Med Chem. 2006 Aug 1;14(15):5370-83. doi: 10.1016/j.bmc.2006.03.039. Epub 2006 Apr 17.

Abstract

To identify potent and selective calcium-release-activated calcium (CRAC) channel inhibitors, we examined the structure-activity relationships of the pyrazole and thiophene moieties in compound 4. Compound 25b was found to exhibit highly potent and selective inhibitory activity for CRAC channels and further modifications of the pyrazole and benzoyl moieties of compound 25b produced compound 29. These compounds were potent inhibitors of IL-2 production in vitro and also acted as inhibitors in pharmacological models of diseases resulting from T-lymphocyte activation, after oral administration.

MeSH terms

  • Animals
  • Calcium / metabolism
  • Calcium Channel Blockers / chemical synthesis*
  • Calcium Channel Blockers / chemistry
  • Calcium Channel Blockers / pharmacology*
  • Calcium Channels / drug effects*
  • Cell Line, Tumor
  • Chemical and Drug Induced Liver Injury / prevention & control
  • Concanavalin A / chemistry
  • Crystallography, X-Ray
  • Disease Models, Animal
  • Drug Evaluation, Preclinical
  • Female
  • Humans
  • Hypersensitivity / prevention & control
  • Jurkat Cells
  • Male
  • Mice
  • Mice, Inbred BALB C
  • Models, Molecular
  • Molecular Structure
  • Picryl Chloride / chemistry
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Calcium Channel Blockers
  • Calcium Channels
  • Pyrazoles
  • Concanavalin A
  • Calcium
  • Picryl Chloride