Novel antagonists of 5-HT3 receptors. Synthesis and biological evaluation of piperazinylquinoxaline derivatives

J Med Chem. 1993 Sep 17;36(19):2745-50. doi: 10.1021/jm00071a005.

Abstract

A series of piperazinylquinoxalines has been synthesized and studied as 5-HT3 receptor antagonists in different preparations. Antagonism to 5-HT in the longitudinal muscle of the guinea pig ileum was particularly prominent in cyanoquinoxaline derivatives with an alkyl substitutuent on the piperazine moiety. The pA2 of some selected compounds against the 5-HT3 agonist 2-methyl-5HT in the guinea pig ileum was in the range of tropisetron or ondansetron, and one of them, 7e, was more potent than these reference compounds by approximately 2 or 3 orders of magnitude. However, these compounds were markedly less potent than either tropisetron or ondansetron as displacers of 3H-BRL 43694 binding to rat cortical membranes or as antagonists of the Bezold-Jarisch reflex in rats. Piperazinylcyanoquinoxalines represent a new class of 5-HT3 antagonists with a selective effect on guinea pig peripheral receptors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Brain / drug effects
  • Brain / metabolism
  • Female
  • Guinea Pigs
  • Male
  • Muscle Contraction / drug effects
  • Muscle, Smooth / drug effects
  • Piperazines / chemical synthesis*
  • Piperazines / pharmacology*
  • Quinoxalines / chemical synthesis*
  • Quinoxalines / pharmacology*
  • Rats
  • Rats, Sprague-Dawley
  • Rats, Wistar
  • Serotonin Antagonists*
  • Structure-Activity Relationship

Substances

  • Piperazines
  • Quinoxalines
  • Serotonin Antagonists