Novel tetracyclic spiropiperidines. 3. 1-arylspiro[indoline-3,4'-piperidine]s as potential antidepressants

J Med Chem. 1983 Jul;26(7):981-6. doi: 10.1021/jm00361a009.

Abstract

A series of 1-arylspiro[indoline-3,4'-piperidine]s was synthesized and evaluated for potential antidepressant activity by tetrabenazine (TBZ) ptosis prevention and potentiation of 5-hydroxytryptophan (5-HTP) induced head twitching in pargyline-pretreated rats. Marked TBZ activity was observed with analogues bearing an ortho substituent on the pendant aromatic ring, as exemplified by lead compound 25a, 1-(2-chlorophenyl)spiro[indoline-3,4'-piperidine], which was also very active in potentiating 5-HTP stereotypy and yohimbine toxicity, as well as in inhibiting the muricidal behavior in rats. The potent in vivo activity of 25a, coupled with weak to moderate in vitro activity with respect to the blockade of neuronal reuptake of biogenic amines, seems to suggest a profile atypical of tricyclic antidepressants.

Publication types

  • Comparative Study

MeSH terms

  • 5-Hydroxytryptophan / pharmacology
  • Animals
  • Antidepressive Agents / chemical synthesis*
  • Biological Assay
  • Blepharoptosis / physiopathology
  • Drug Synergism
  • Humans
  • Indicators and Reagents
  • Indoles / chemical synthesis*
  • Indoles / pharmacology
  • Piperidines / chemical synthesis*
  • Piperidines / pharmacology
  • Stereotyped Behavior / drug effects
  • Structure-Activity Relationship
  • Tetrabenazine / toxicity

Substances

  • Antidepressive Agents
  • Indicators and Reagents
  • Indoles
  • Piperidines
  • 5-Hydroxytryptophan
  • Tetrabenazine