Novel, potent, and selective quinoxaline-based 5-HT(3) receptor ligands. 1. Further structure-activity relationships and pharmacological characterization

J Med Chem. 2009 Nov 12;52(21):6946-50. doi: 10.1021/jm901126m.

Abstract

We investigated the pharmacological profile of a novel series of quinoxaline-based 5-HT(3) receptor ligands bearing an extra basic moiety on the piperazine N-4. High affinity and selectivity were dependent on the electronic properties of the substituents, and at cardiac level 3a and 3c modulated chronotropy but not inotropy. In von Bezold-Jarisch reflex test 3a-c were partial agonists while 3i was a full agonist. Preliminary pharmacokinetic studies indicated that 3a is a brain penetrating agent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Blood-Brain Barrier / metabolism
  • Drug Partial Agonism
  • Guinea Pigs
  • Heart Rate / drug effects
  • In Vitro Techniques
  • Ligands
  • Myocardial Contraction / drug effects
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Pyrroles / pharmacology
  • Quinoxalines / chemical synthesis*
  • Quinoxalines / pharmacokinetics
  • Quinoxalines / pharmacology
  • Rats
  • Reflex / drug effects
  • Serotonin 5-HT3 Receptor Agonists*
  • Serotonin 5-HT3 Receptor Antagonists
  • Structure-Activity Relationship

Substances

  • Ligands
  • Pyrroles
  • Quinoxalines
  • Serotonin 5-HT3 Receptor Agonists
  • Serotonin 5-HT3 Receptor Antagonists