Aminimides as Potential CNS Acting Agents. II Design, Synthesis, and Receptor Binding of 4′-Arylalkyl Aminimide Analogues of Clozapine as Prospective Novel Antipsychotics

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Contents Vol 61(1)

doi:10.1071/CH07275

Aminimides as Potential CNS Acting Agents. II* Design, Synthesis, and Receptor Binding of 4′-Arylalkyl Aminimide Analogues of Clozapine as Prospective Novel Antipsychotics

Ben Capuano ^A, Ian T. Crosby ^A ^D, Edward J. Lloyd ^A, Juliette E. Neve ^A ^B, David A. Taylor ^C

^A Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, 381 Royal Parade, Parkville VIC 3052, Australia.
^B Current address: Natural Product Discovery, Eskitis Institute for Cell and Molecular Therapies, Griffith University, Nathan QLD 4111, Australia.
^C Department of Pharmaceutical Biology, Victorian College of Pharmacy, Monash University, 381 Royal Parade, Parkville VIC 3052, Australia.
^D Corresponding author. Email: ian.crosby@vcp.monash.edu.au





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Australian Journal of Chemistry 61(1) 5–10 http://dx.doi.org/10.1071/CH07275
Submitted: 3 August 2007 Accepted: 30 October 2007 Published online: 18 January 2008

Abstract

We report the synthesis of a series of second generation aminimide-based analogues of clozapine, investigating the length of the linker between the aminimide functional group and the introduced aryl moiety. The chemistry and structural characterization of this series of 4′-arylalkyl aminimide analogues of clozapine are described. Preliminary findings on the biochemical effects of linker length and type of aryl moiety on affinity for dopamine D₄ and serotonin 5-HT_2A receptors are discussed. All of the compounds showed a marked reduction in binding at the two receptors when compared with clozapine, thus showing a reduced potential for atypical antipsychotic activity.

^* Part I, Aust. J. Chem. 2007, 60, 673.