Synthesis of carbamide derivatives bearing tetrahydroisoquinoline moieties and biological evaluation as analgesia drugs in mice

Arch Pharm (Weinheim). 2015 May;348(5):347-52. doi: 10.1002/ardp.201400455. Epub 2015 Mar 30.

Abstract

Transient receptor potential vanilloid 1 (TRPV1) is a ligand-gated non-selective cation channel that is considered to be an important pain integrator. Tetrahydroisoquinoline, the prototypical antagonist of TRPV1, has a clear therapeutic potential. Here, a series of carbamide derivatives of tetrahydroisoquinoline were designed and synthesized. Preliminary biological tests suggested that the compounds I 1, I 2, and I 9 had favorable TRPV1 antagonism activity. In further studies, I 1 exhibited better antinociceptive activity than the positive control BCTC in diverse pain models. All of these results suggested that I 1 can be considered as the lead candidate for the further development of antinociceptive drugs.

Keywords: Analgesia drugs; Tetrahydroisoquinoline derivatives; Transient receptor potential vanilloid 1 antagonist.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Analgesics / chemical synthesis*
  • Analgesics / pharmacology*
  • Animals
  • Behavior, Animal / drug effects
  • Cells, Cultured
  • Disease Models, Animal
  • Dose-Response Relationship, Drug
  • Drug Design
  • Mice
  • Molecular Structure
  • Nociception / drug effects
  • Pain / etiology
  • Pain / metabolism
  • Pain / physiopathology
  • Pain / prevention & control*
  • Pain / psychology
  • Structure-Activity Relationship
  • TRPV Cation Channels / antagonists & inhibitors*
  • TRPV Cation Channels / metabolism
  • Tetrahydroisoquinolines / chemical synthesis*
  • Tetrahydroisoquinolines / pharmacology*
  • Urea / analogs & derivatives
  • Urea / chemical synthesis*
  • Urea / pharmacology*

Substances

  • Analgesics
  • TRPV Cation Channels
  • TRPV1 protein, mouse
  • Tetrahydroisoquinolines
  • Urea