Benzimidazole derivatives. Part 5: design and synthesis of new benzimidazole-arylpiperazine derivatives acting as mixed 5-HT1A/5-HT3 ligands

Bioorg Med Chem. 2004 Oct 1;12(19):5181-91. doi: 10.1016/j.bmc.2004.07.023.

Abstract

A series of new mixed benzimidazole-arylpiperazine derivatives were designed by incorporating in general structure III the pharmacophoric elements of 5-HT(1A) and 5-HT(3) receptors. Compounds 1-11 were synthesized and evaluated for binding affinity at both serotoninergic receptors, all of them exhibiting high 5-HT(3)R affinity (K(i)=10-62nM), and derivatives with an o-alkoxy group in the arylpiperazine ring showing nanomolar affinity for the 5-HT(1A)R (K(i)=18-150nM). Additionally, all the synthesized compounds were selective over alpha(1)-adrenergic and dopamine D(2) receptors (K(i)>1000-10,000nM). Compound 3 was selected for further pharmacological characterization due to its interesting binding profile as mixed 5-HT(1A)/5-HT(3) ligand with high affinity for both receptors (5-HT(1A): K(i)=18.0nM, 5-HT(3): K(i)=27.2nM). In vitro and in vivo findings suggest that this compound acts as a partial agonist at 5-HT(1A)Rs and as a 5-HT(3)R antagonist. This novel mixed 5-HT(1A)/5-HT(3) ligand was also effective in preventing the cognitive deficits induced by muscarinic receptor blockade in a passive avoidance learning test, suggesting a potential interest in the treatment of cognitive dysfunction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Avoidance Learning / drug effects
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / pharmacology
  • Cognition Disorders / drug therapy
  • Guanosine 5'-O-(3-Thiotriphosphate) / chemistry
  • Guanosine 5'-O-(3-Thiotriphosphate) / metabolism
  • Guinea Pigs
  • Hippocampus / metabolism
  • Hypothermia / chemically induced
  • Ligands
  • Male
  • Mice
  • Muscle Contraction / drug effects
  • Piperazines / chemical synthesis*
  • Piperazines / pharmacology
  • Rats
  • Rats, Wistar
  • Serotonin 5-HT1 Receptor Antagonists
  • Serotonin 5-HT3 Receptor Antagonists
  • Serotonin Antagonists / chemical synthesis*
  • Serotonin Antagonists / pharmacology
  • Structure-Activity Relationship

Substances

  • Benzimidazoles
  • Ligands
  • Piperazines
  • Serotonin 5-HT1 Receptor Antagonists
  • Serotonin 5-HT3 Receptor Antagonists
  • Serotonin Antagonists
  • Guanosine 5'-O-(3-Thiotriphosphate)