Novel 5-HT7R antagonists, arylsulfonamide derivatives of (aryloxy)propyl piperidines: Add-on effect to the antidepressant activity of SSRI and DRI, and pro-cognitive profile

Bioorg Med Chem. 2017 May 15;25(10):2789-2799. doi: 10.1016/j.bmc.2017.03.057. Epub 2017 Mar 29.

Abstract

A novel series of arylsulfonamide derivatives of (aryloxy)propyl piperidines was designed to obtain potent 5-HT7R antagonists. Among the compounds evaluated herein, 3-chloro-N-{1-[3-(1,1-biphenyl-2-yloxy)2-hydroxypropyl]piperidin-4-yl}benzenesulfonamide (25) exhibited antagonistic properties at 5-HT7R and showed selectivity over selected serotoninergic and dopaminergic receptors, as well as over serotonin, noradrenaline and dopamine transporters. Compound 25 demonstrated significant antidepressant-like activity in the forced swim test (0.625-2.5mg/kg, i.p.) and in the tail suspension test (1.25mg/kg, i.p.), augmented the antidepressant effect of inactive doses of escitalopram (selective serotonin reuptake inhibitor) and bupropion (dopamine reuptake inhibitor) in the FST in mice, and similarly to SB-269970, exerted pro-cognitive properties in the novel object recognition task in cognitively unimpaired conditions in rats (0.3mg/kg, i.p.). Such an extended pharmacological profile, especially the augmentation effect of the identified 5-HT7R antagonist on SSRI activity, seems promising regarding the complexity of affective disorders and potentially improved outcomes, including mnemonic performance.

Keywords: 5-HT(7) antagonist; Cognitive deficit; Depression; Dopamine reuptake inhibitor; Selectivity prediction; Serotonin reuptake inhibitor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antidepressive Agents / chemical synthesis
  • Antidepressive Agents / chemistry*
  • Antidepressive Agents / pharmacology
  • Behavior, Animal / drug effects
  • Binding Sites
  • CHO Cells
  • Cognition / drug effects
  • Cricetinae
  • Cricetulus
  • Dopamine Uptake Inhibitors / chemistry*
  • Dopamine Uptake Inhibitors / pharmacology
  • HEK293 Cells
  • Humans
  • Mice
  • Mice, Inbred C57BL
  • Molecular Docking Simulation
  • Phenols / pharmacology
  • Piperidines / chemistry*
  • Protein Structure, Tertiary
  • Rats
  • Receptors, Serotonin / chemistry*
  • Receptors, Serotonin / genetics
  • Receptors, Serotonin / metabolism
  • Selective Serotonin Reuptake Inhibitors / chemistry*
  • Selective Serotonin Reuptake Inhibitors / pharmacology
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacology

Substances

  • Antidepressive Agents
  • Dopamine Uptake Inhibitors
  • Phenols
  • Piperidines
  • Receptors, Serotonin
  • SB 269970
  • Serotonin Uptake Inhibitors
  • Sulfonamides
  • serotonin 7 receptor