Issue 24, 2014
From the journal:

Organic & Biomolecular Chemistry

Synthesis and antimalarial activity of prodigiosenes†

Estelle Marchal,a   Deborah A. Smithen,a   Md. Imam Uddin,a   Andrew W. Robertson,a   David L. Jakeman,ab   Vanessa Mollard,c   Christopher D. Goodman,c   Kristopher S. MacDougall,d   Sherri A. McFarland,*d   Geoffrey I. McFadden*c  and  Alison Thompson*a  

* Corresponding authors

a Department of Chemistry, Dalhousie University, PO BOX 15000, Halifax, NS, Canada
E-mail: Alison.Thompson@dal.ca
Tel: +1-902-494-3305

b College of Pharmacy, Dalhousie University, PO Box 15000, Halifax, NS, Canada

c School of Botany, University of Melbourne, VIC 3010, Australia
E-mail: gim@unimelb.edu.au
Tel: +61 414 189 905

d Department of Chemistry, Acadia University, Wolfville, Nova Scotia, Canada
E-mail: sherri.mcfarland@acadiau.ca
Tel: +1-902-585-1320

Abstract

Several analogues of the natural compound prodigiosin with modified A- and C-rings were synthesised as were some of their tin, cobalt, boron and zinc complexes. The antimalarial activity of these prodigiosenes was evaluated in vitro using the 3D7 Plasmodium falciparum strain. The presence of a nitrogen atom in the A-ring is needed for antimalarial activity but the presence of an alkyl group at the β′-position of the C-ring seems detrimental. Dibutyl tin complexes exhibit IC50 values mostly in the nanomolar range with equal or improved activity compared to the free-base prodigiosene ligand, despite the fact that the general toxicity of such tin complexes is demonstrably lower than that of the free-bases.

Graphical abstract: Synthesis and antimalarial activity of prodigiosenes

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Article information

DOI
https://doi.org/10.1039/C3OB42548G
Article type
Paper
Submitted
20 Dec 2013
Accepted
06 May 2014
First published
16 May 2014

Org. Biomol. Chem., 2014,12, 4132-4142

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Synthesis and antimalarial activity of prodigiosenes

E. Marchal, D. A. Smithen, Md. I. Uddin, A. W. Robertson, D. L. Jakeman, V. Mollard, C. D. Goodman, K. S. MacDougall, S. A. McFarland, G. I. McFadden and A. Thompson, Org. Biomol. Chem., 2014, 12, 4132 DOI: 10.1039/C3OB42548G

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