The Synthesis and Biological Evaluation of Two Analogues of the C-Riboside Showdomycin

Jens Renner; Irma Kruszelnicki; Beata Adamiak; Anthony C. Willis; Edward Hammond; Stephen Su; Christopher Burns; Edward Trybala; Vito Ferro; Martin G. Banwell

doi:10.1071/CH04273

RESEARCH ARTICLE

The Synthesis and Biological Evaluation of Two Analogues of the C-Riboside Showdomycin

Jens Renner ^A , Irma Kruszelnicki ^B , Beata Adamiak ^C , Anthony C. Willis ^A , Edward Hammond ^D , Stephen Su ^B , Christopher Burns ^B , Edward Trybala ^C , Vito Ferro ^D and Martin G. Banwell ^A ^E

+ Author Affiliations

- Author Affiliations

^A Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra ACT 0200, Australia.

^B Cytopia Pty Ltd, Baker Heart Research Institute, Commercial Road, Melbourne VIC 3004, Australia.

^C Department of Clinical Virology, Göteborg University, 413 46 Göteborg, Sweden.

^D Drug Design Group, Progen Industries Ltd, 2806 Ipswich Road, Darra QLD 4076, Australia.

^E Corresponding author. Email: mgb@rsc.anu.edu.au

Australian Journal of Chemistry 58(2) 86-93 https://doi.org/10.1071/CH04273
Submitted: 15 November 2004 Accepted: 13 January 2005 Published: 21 February 2005

Abstract

Two novel analogues, 2 and 3, of the C-riboside showdomycin (1) have been prepared by exploiting the N-TIPS-substituted pyrrole 7 as a synthetic equivalent for the maleimide C3 anion. The tetraacetate precursor, 12, of target 2 as well as target 3 itself were subjected to single-crystal X-ray analyses. Analogues 2 and 3 as well as showdomycin and its anomer (4) have each been evaluated in various assays for their cytotoxic, anti-bacterial, and anti-viral effects.

Acknowledgments

This work was generously supported by Progen Industries Ltd and the Institute of Advanced Studies (Australian National University). We thank the Alexander von Humboldt Foundation for providing a Feodor Lynen Fellowship to J.R. Dr Gregg Whited (Genencor International Inc., Palo Alto, CA) is gratefully acknowledged for providing us with generous quantities of cis-1,2-dihydrocatechol 13. Dr Natasha Hungerford is warmly thanked for preparing samples of showdomycin (1) and its anomer (4). We are also grateful to Dr Alison Edwards for carrying out a single-crystal X-ray analysis of compound 12.

References

The Synthesis and Biological Evaluation of Two Analogues of the C-Riboside Showdomycin

Abstract

Acknowledgments

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