Synthesis of 2-piperazinylbenzothiazole and 2-piperazinylbenzoxazole derivatives with 5-HT3 antagonist and 5-HT4 agonist properties

J Med Chem. 1994 Apr 29;37(9):1320-5. doi: 10.1021/jm00035a012.

Abstract

New 2-piperazinylbenzothiazole and 2-piperazinylbenzoxazole derivatives were prepared and tested as 5-HT3 receptor antagonists. Some of the new compounds antagonized the effect of 5-HT at the longitudinal muscle myenteric plexus (LMMP) preparation of the guinea pig ileum, and two benzothiazole derivatives, compounds 2e and 2f, were more potent than ondansetron in this regard. However, these two compounds were much weaker than the typical 5-HT3 receptor antagonist as displacers of [3H]BRL-43694 binding to rat cerebral cortex homogenates or as antagonists of the bradycardia response to 5-HT in the anaesthetized rat. Like the prokinetic agent cisapride, some of the new compounds enhanced gastric emptying in rats. Compound 2f not only markedly enhanced gastric emptying but was also a potent agonist at the isolated rat oesophageal tunica muscularis mucosae, a preparation sensitive to 5-HT4 receptor stimulation, and enhanced the twitch response in the LMMP preparation. The latter effect was blocked by a high concentration of tropisetron or by previous desensitization with 5-methoxytryptamine. Compound 2f appears to show a promising pharmacological profile as a potential gastrokinetic agent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzothiazoles
  • Binding, Competitive
  • Cerebral Cortex / metabolism
  • Female
  • Gastric Emptying / drug effects
  • Granisetron / metabolism
  • Guinea Pigs
  • Ileum / drug effects
  • Ileum / physiology
  • Male
  • Molecular Structure
  • Mucous Membrane / drug effects
  • Mucous Membrane / physiology
  • Ondansetron / pharmacology
  • Piperazines / chemical synthesis*
  • Piperazines / pharmacology
  • Rats
  • Rats, Sprague-Dawley
  • Rats, Wistar
  • Serotonin / pharmacology
  • Serotonin Antagonists / chemical synthesis*
  • Serotonin Antagonists / pharmacology
  • Serotonin Receptor Agonists / chemical synthesis*
  • Serotonin Receptor Agonists / pharmacology
  • Thiazoles / chemical synthesis*
  • Thiazoles / pharmacology

Substances

  • Benzothiazoles
  • Piperazines
  • Serotonin Antagonists
  • Serotonin Receptor Agonists
  • Thiazoles
  • 2-(1-(4-piperonyl)piperazinyl)benzothiazole
  • Serotonin
  • Ondansetron
  • Granisetron