Reaction Pathways to 2-Aminothiophenes and Thiophene-3-carbonitriles

Luigi Aurelio; Bernard L. Flynn; Peter J. Scammells

doi:10.1071/CH09004

RESEARCH ARTICLE

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Reaction Pathways to 2-Aminothiophenes and Thiophene-3-carbonitriles

Luigi Aurelio ^A , Bernard L. Flynn ^A and Peter J. Scammells ^A ^B

+ Author Affiliations

- Author Affiliations

^A Medicinal Chemistry and Drug Action, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville, Vic. 3052, Australia.

^B Corresponding author. Email: peter.scammells@pharm.monash.edu.au

Australian Journal of Chemistry 62(5) 402-406 https://doi.org/10.1071/CH09004
Submitted: 5 January 2009 Accepted: 10 February 2009 Published: 15 May 2009

Abstract

Over the past two decades 2-amino-3-benzoylthiophenes have been found to act as allosteric enhancers of the adenosine A₁ receptor (A₁AR). As such, compounds of this type have potential applications in the therapy of a variety of disorders by enhancing A₁AR activation. Initial studies in this field identified various 2-amino-3-benzoylthiophenes as potential leads and of these PD 81723 1a has become the benchmark for comparative studies due to its favourable ratio of allosteric enhancement to antagonism. Surprisingly the synthesis and characterization of PD 81723 1a has not been previously reported. Herein we report the synthesis and characterization of this important A₁AR allosteric enhancer. As part of this study we also found an unexpected reaction pathway to 2-phenylthiophene-3-carbonitriles.

Acknowledgements

The authors thank the Australian Research Council (DP0877497) for financial support.

References

Reaction Pathways to 2-Aminothiophenes and Thiophene-3-carbonitriles

Abstract

Acknowledgements

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