Aminimides as Potential CNS-Acting Agents. III. Design, Synthesis, and Receptor Binding of Aminimide Analogues of Dopamine, Serotonin, Morphine, and Nicotine

Ben Capuano; Ian T. Crosby; Edward J. Lloyd; Juliette E. Neve; David A. Taylor

doi:10.1071/CH08060

RESEARCH ARTICLE

Previous Next Contents Vol 61(6)

Aminimides as Potential CNS-Acting Agents. III. Design, Synthesis, and Receptor Binding of Aminimide Analogues of Dopamine, Serotonin, Morphine, and Nicotine

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

+ Author Affiliations

- Author Affiliations

^A Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, 381 Royal Parade, Parkville VIC 3052, Australia.

^B Present address: 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

Australian Journal of Chemistry 61(6) 422-431 https://doi.org/10.1071/CH08060
Submitted: 14 February 2008 Accepted: 23 April 2008 Published: 19 June 2008

Abstract

A series of aminimide derivatives of centrally acting agents, namely dopamine, serotonin, morphine and nicotine, were designed on the basis of the physicochemical properties of the aminimide functional group and synthesized to investigate their central nervous system (CNS) receptor affinity. The target compounds were readily prepared from an appropriate tertiary amine by N-acylation of a hydrazinium salt intermediate using acetic anhydride or acetyl chloride. The aminimides were tested for in vitro affinity at the dopaminergic D₄, serotonergic 5-HT_2A, opiate (μ, κ, and non-selective) and nicotinic acetylcholine receptors and were found to possess mixed affinities for the aforementioned receptor systems.

Acknowledgement

The receipt of a Monash Graduate Scholarship (J.E.N.) for support of the present research is acknowledged.

References

Aminimides as Potential CNS-Acting Agents. III. Design, Synthesis, and Receptor Binding of Aminimide Analogues of Dopamine, Serotonin, Morphine, and Nicotine

Abstract

Acknowledgement

Subscriber Login