Synthesis of new aryl(hetaryl)-substituted tandospirone analogues with potential anxiolytic activity via reductive Heck type hydroarylations


GÜNKARA Ö. T. , Sucu B. O. , Ocal N. , Kaufmann D. E.

CHEMICAL PAPERS, vol.67, no.6, pp.643-649, 2013 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 67 Issue: 6
  • Publication Date: 2013
  • Doi Number: 10.2478/s11696-013-0338-4
  • Title of Journal : CHEMICAL PAPERS
  • Page Numbers: pp.643-649
  • Keywords: tandospirone, arylpiperazines, C-C coupling, hydroarylation, heterocycles, SUBSTITUTED TRICYCLIC IMIDES, DOPAMINE D3 RECEPTOR, UNSATURATED DICARBOXIMIDES, PHARMACOLOGICAL AGENTS, EPIBATIDINE, DERIVATIVES, CHEMISTRY, AFFINITY, NUCLEUS, AGONIST

Abstract

Tandospirone (I), developed as an anxiolytic drug, is an aryl-piperazine compound that binds to both 5-HT1A and dopamine D4 receptors. Palladium-catalysed hydroarylation reactions of tandospirone analogues containing an oxygen bridge and 3-(trifluoromethyl)phenyl or 2,3-dichlorophenyl groups were studied in order to find a new stereoselective access to a series of new exo-aryl(hetaryl)-substituted derivatives with potential biological activity.