Design, synthesis, and biological evaluation of phenylpropanamides as novel transient receptor potential vanilloid 1 antagonists

Arch Pharm Res. 2009 Sep;32(9):1201-10. doi: 10.1007/s12272-009-1903-9. Epub 2009 Sep 26.

Abstract

Synthesis and structure-activity relationship of N-benzyl-3-phenylpropanamides as transient receptor potential vanilloid 1 (TRPV1) antagonists are described. A variety of substituents such as halide, ester, nitro, and alkyl groups at 2 or 3-position of 4-(methylsulfonylamino) benzyl unit were examined. These compounds exhibited potent 45Ca2+ uptake inhibition in rat DRG neuron via TRPV1 blockade. Especially compound 28c, has been identified as a potent antagonist with IC50 of 38 nM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / pharmacology
  • Animals
  • Calcium / metabolism
  • Cells, Cultured
  • Drug Design
  • Ganglia, Spinal / drug effects
  • Ganglia, Spinal / metabolism
  • Rats
  • Rats, Sprague-Dawley
  • TRPV Cation Channels / antagonists & inhibitors*

Substances

  • Amides
  • TRPV Cation Channels
  • TRPV1 receptor
  • Calcium