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Article << Previous     |     Next >>   Contents Vol 65(12)

Probing for the Pharmacophore of the Cytotoxic Neoclerodane Salvileucalin B

Nora Heinrich A , Martin G. Banwell A C , Anthony C. Willis A , Ian A. Cade A , Robert J. Capon B and Xiao-Cong Huang B

A Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.
B Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland, St Lucia, Qld 4072, Australia.
C Corresponding author. Email: mgb@rsc.anu.edu.au

Australian Journal of Chemistry 65(12) 1679-1686 http://dx.doi.org/10.1071/CH12358
Submitted: 31 July 2012  Accepted: 31 August 2012   Published: 31 October 2012

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The novel [4.3.1]propelladiene 2, which embodies the key structural elements of the pentacyclic core of the cytotoxic neoclerodane salvileucalin B (1), has been prepared using a rhodium-catalysed intramolecular Büchner reaction as the key step. Compound 2 and the readily obtained derivatives 1217 all proved to be essentially inactive when tested against a panel of four human cancer cell lines. Furthermore, not one of these compounds was a P-gp inhibitor.


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