Efficient Large-Scale Synthesis of CAT811, a Potent Calpain Inhibitor of Interest in the Treatment of Cataracts

Matthew A. Jones; James M. Coxon; Stephen B. McNabb; Janna M. Mehrtens; Nathan A. Alexander; Seth Jones; Hongyuan Chen; Clémence Buisan; Andrew D. Abell

doi:10.1071/CH09101

RESEARCH FRONT

Efficient Large-Scale Synthesis of CAT811, a Potent Calpain Inhibitor of Interest in the Treatment of Cataracts

Matthew A. Jones ^A , James M. Coxon ^A , Stephen B. McNabb ^A , Janna M. Mehrtens ^A , Nathan A. Alexander ^A , Seth Jones ^B , Hongyuan Chen ^A , Clémence Buisan ^A and Andrew D. Abell ^B ^C

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, University of Canterbury, Christchurch, Private Bag 4800, New Zealand.

^B School of Chemistry and Physics, University of Adelaide, North Terrace, Adelaide, SA 5005, Australia.

^C Corresponding author. Email: andrew.abell@adelaide.edu.au

Australian Journal of Chemistry 62(7) 671-675 https://doi.org/10.1071/CH09101
Submitted: 19 February 2009 Accepted: 31 March 2009 Published: 13 July 2009

Abstract

A high-yielding, short, and scalable synthesis of a potent calpain 2 inhibitor (CAT811) is reported. The key step in the sequence involves an intramolecular macrocyclization of a 6-iodonorleucine residue to the side chain of tyrosine.

Acknowledgements

Financial support from New Zealand Public Good Science and Technology Fund, New Zealand Foundation for Research Science and Technology, Australian Research Council, and Douglas Pharmaceuticals Limited is gratefully acknowledged.

References

Efficient Large-Scale Synthesis of CAT811, a Potent Calpain Inhibitor of Interest in the Treatment of Cataracts

Abstract

Acknowledgements

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