Synthesis of 1-arylpiperazyl-2-phenylcyclopropanes designed as antidopaminergic agents: cyclopropane-based conformationally restricted analogs of haloperidol.

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Yamaguchi K, Kazuta Y, Hirano K, Yamada S, Matsuda A, Shuto S

Synthesis of 1-arylpiperazyl-2-phenylcyclopropanes designed as antidopaminergic agents: cyclopropane-based conformationally restricted analogs of haloperidol.

Bioorg Med Chem. 2008 Oct 1;16(19):8875-81. doi: 10.1016/j.bmc.2008.08.061. Epub 2008 Aug 29.

PubMed ID
18793859 [ View in PubMed
]
Abstract

A series of the cyclopropane-based conformationally restricted analogs of haloperidol were designed as potential antidopaminergic agents and were effectively synthesized using highly stereoselective Grignard reaction with tert-butanesulfinyl imines as the key step. Pharmacological evaluation of the compounds showed that the conformational restriction method can effectively work for improving the pharmacological selectivity of a parent compound and also for investigating the bioactive conformation.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
HaloperidolDopamine D2 receptorKi (nM)5.09N/AN/ADetails