Novel potent and selective calcium-release-activated calcium (CRAC) channel inhibitors. Part 1: synthesis and inhibitory activity of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-2-thiophenecarboxamides

Bioorg Med Chem. 2006 Jul 15;14(14):4750-60. doi: 10.1016/j.bmc.2006.03.024. Epub 2006 Mar 31.

Abstract

We synthesized and evaluated a series of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-2-thiophenecarboxamides to identify potent inhibitors of calcium-release-activated calcium (CRAC) channels with greater selectivity than voltage-operated calcium (VOC) channels. These efforts resulted in identification of compounds 22 and 24. The former exhibits highly potent and selective CRAC channel inhibitory activity, and the latter inhibited phytohemagglutinin-induced interleukin-2 production by Jurkat T lymphocytes and concanavalin A-induced hepatitis in mice.

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amides / pharmacology*
  • Animals
  • Calcium Channel Blockers / chemical synthesis*
  • Calcium Channel Blockers / chemistry
  • Calcium Channel Blockers / pharmacology*
  • Calcium Channels / drug effects
  • Calcium Channels / metabolism
  • Drug Evaluation, Preclinical
  • Female
  • Humans
  • Interleukin-2 / biosynthesis
  • Jurkat Cells
  • Mice
  • Mice, Inbred BALB C
  • PC12 Cells
  • Quantitative Structure-Activity Relationship
  • Rats
  • Thiophenes / chemical synthesis*
  • Thiophenes / chemistry
  • Thiophenes / pharmacology*

Substances

  • Amides
  • Calcium Channel Blockers
  • Calcium Channels
  • Interleukin-2
  • Thiophenes