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

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Contents Vol 58(2)

doi:10.1071/CH04273

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, Martin G. Banwell ^A ^E

^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





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Australian Journal of Chemistry 58(2) 86–93 http://dx.doi.org/10.1071/CH04273
Submitted: 15 November 2004 Accepted: 13 January 2005 Published online: 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.