Synthesis and biological evaluation of 1-(1,2-benzisothiazol-3-yl)- and (1,2-benzisoxazol-3-yl)piperazine derivatives as potential antipsychotic agents

J Med Chem. 1986 Mar;29(3):359-69. doi: 10.1021/jm00153a010.

Abstract

Members of the series of title compounds were tested for potential antipsychotic activity in relevant receptor binding assays and behavioral screens. Structure-activity relationships within the series are discussed. Compound 24 (BMY 13859-1), a (1,2-benzisothiazol-3-yl)piperazine derivative, was selected for further study because of its potent and selective profile in primary CNS tests. It was active in the Sidman avoidance paradigm and blocked amphetamine-induced stereotyped behavior in dogs for up to 7 h. The compound's lack of typical neuroleptic-like effects in the rat catalepsy test and its failure to produce dopamine receptor supersensitivity following chronic administration indicate that it should not cause the movement disorders commonly associated with antipsychotic therapy. Although 24 has potent affinity for dopaminergic binding sites, its even greater affinity for serotonin receptors suggests that a serotonergic component may be relevant to its atypical profile. Compound 24 is currently undergoing clinical evaluation in schizophrenic patients.

MeSH terms

  • Animals
  • Antipsychotic Agents / chemical synthesis*
  • Avoidance Learning / drug effects
  • Binding, Competitive
  • Catalepsy / chemically induced
  • Cerebral Cortex / metabolism
  • Corpus Striatum / metabolism
  • Isoxazoles / chemical synthesis*
  • Isoxazoles / pharmacology
  • Male
  • Models, Molecular
  • Norepinephrine / antagonists & inhibitors
  • Oxazoles / chemical synthesis*
  • Physostigmine / antagonists & inhibitors
  • Piperazines / chemical synthesis*
  • Piperazines / pharmacology
  • Rats
  • Rats, Inbred Strains
  • Receptors, Adrenergic, alpha / metabolism
  • Receptors, Dopamine / metabolism
  • Receptors, Dopamine D2
  • Receptors, Serotonin / drug effects
  • Sleep / drug effects
  • Spiro Compounds / pharmacology
  • Stereotyped Behavior / drug effects
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis*
  • Thiazoles / pharmacology

Substances

  • Antipsychotic Agents
  • Isoxazoles
  • Oxazoles
  • Piperazines
  • Receptors, Adrenergic, alpha
  • Receptors, Dopamine
  • Receptors, Dopamine D2
  • Receptors, Serotonin
  • Spiro Compounds
  • Thiazoles
  • tiospirone
  • Physostigmine
  • Norepinephrine