Pyrazolopyrimidines as Potent Stimulators for Transient Receptor Potential Canonical 3/6/7 Channels

J Med Chem. 2017 Jun 8;60(11):4680-4692. doi: 10.1021/acs.jmedchem.7b00304. Epub 2017 Apr 28.

Abstract

Transient receptor potential canonical 3/6/7 (TRPC3/6/7) are highly homologous receptor-operated nonselective cation channels. Despite their physiological significance, very few selective and potent agonists are available for functional examination of these channels. Using a cell-based high throughput screening approach, a lead compound with the pyrazolopyrimidine skeleton was identified as a TRPC6 agonist. Synthetic schemes for the lead and its analogues were established, and structural-activity relationship studies were carried out. A series of potent and direct agonists of TRPC3/6/7 channels were identified, and among them, 4m-4p have a potency order of TRPC3 > C7 > C6, with 4n being the most potent with an EC50 of <20 nM on TRPC3. Importantly, these compounds exhibited no stimulatory activity on related TRP channels. The potent and selective compounds described here should be suitable for evaluation of the roles of TRPC channels in the physiology and pathogenesis of diseases, including glomerulosclerosis and cancer.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, N.I.H., Extramural

MeSH terms

  • HEK293 Cells
  • Humans
  • Pyrazoles / chemistry*
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology*
  • Structure-Activity Relationship
  • TRPC Cation Channels / agonists*
  • TRPC6 Cation Channel

Substances

  • Pyrazoles
  • Pyrimidines
  • TRPC Cation Channels
  • TRPC3 cation channel
  • TRPC6 Cation Channel
  • TRPC6 protein, human
  • TRPC7 protein, human