Discovery of a new class of multi-target heterocycle piperidine derivatives as potential antipsychotics with pro-cognitive effect

Bioorg Med Chem Lett. 2021 May 15:40:127909. doi: 10.1016/j.bmcl.2021.127909. Epub 2021 Mar 9.

Abstract

A series of benzoisoxazoleylpiperidine derivatives were synthesized by using the multi-target strategies and their potent affinities for dopamine (DA), serotonin (5-HT) and human histamine H3 receptors have been evaluated. Of these compounds, the promising candidate 4w displayed high affinities for D2, D3, 5-HT1A, 5-HT2A and H3, a moderate affinity for 5-HT6, negligible effects on the human ether-a-go-go-related gene (hERG) channel, low affinities for off-target receptors (5-HT2C, adrenergic α1 and H1). In addition, the animal behavioral study revealed that, compared to risperidone, compound 4w significantly inhibited apomorphine-induced climbing and MK-801-induced movement behaviors with a high threshold for catalepsy and low liabilities for weight gain and hyperprolactinemia. Results from the conditioned avoidance response test and novel object recognition task demonstrated that 4w had pro-cognitive effects. Thus, the antipsychotic drug-like activities of 4w indicate that it may be a potential polypharmacological antipsychotic candidate drug.

Keywords: Atypical antipsychotics; Cognition; Dopamine; Multi-target; Serotonin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antipsychotic Agents / chemistry*
  • Antipsychotic Agents / pharmacology
  • Behavior, Animal
  • Cognition / drug effects*
  • Dopamine / chemistry
  • Drug Design
  • Humans
  • Hyperprolactinemia / metabolism
  • Mice
  • Models, Animal
  • Movement / drug effects
  • Piperidines / chemistry*
  • Piperidines / pharmacology
  • Protein Binding
  • Receptors, Histamine H3 / chemistry
  • Risperidone / pharmacology
  • Serotonin / chemistry
  • Structure-Activity Relationship
  • Weight Gain

Substances

  • Antipsychotic Agents
  • Piperidines
  • Receptors, Histamine H3
  • Serotonin
  • Risperidone
  • Dopamine